For Love or Money
by ladyand
Summary: 2008 Recession AU. Fearing losing her home Blair strikes a deal she cannot refuse with Charles Bass, her best friend's older step brother. One night with him for the money she needs to stop the bank from seizing their possessions. She agrees never realizing the ramifications of that one night will have for family, friends & her future. A high stake political romance drama. RxR
1. The Great Recession

A.N: I wanted to try to write a more villainous Chuck. Yet somehow his sweet side (in later chapters more so) emerged heavily.

Change in their bios that will be further explained: Blair/Serena are eighteen (and are their last year of high school), Nate is twenty, and Chuck is twenty-two in the beginning of this fic. Chuck and Serena/Eric have been sibling for years Lily having married Bart when the children were younger. Also Nate and Chuck were educated in a boarding school for boys. Also Blair is a estranged from her father. Out of all the character's Blair is the one who is a bit different than the show even still I tried my best to model this off of her character as close as possible.

* * *

January 2009

The Great Recession emptied the bank accounts of many victims and some criminals from Wall Street. Certainly the Upper East Side was feeling the pain of the Stock Market losses. It seemed as if everyone was suffering somehow. In the UES this was shown in the materialism of the upper society. Girls in class who always wore the latest season were instead wearing last winter's coats. Boys who lavishly spent money on watches and cars they never drove lessen their spending. Families who once rented entire islands and yachts were vacationing instead in their second home in the Caribbean or in the Hampton. While others were selling all their second homes at a loss. Surely no one was suffering for food but it was clear to those in St. Jude and in Constance School for Girls who was part of the extremely wealthy one percent and those who slowly falling into the upper middle class. Sadly, for Blair Waldorf she was stumbling into a whole new different class bracket.

Almost four years ago her father left her mother and her with little extra income. Blair still extremely prideful and she often bit her lip as Serena, her best and dearest friend paid for their expensive meals and for clothes whenever her allowance ran out. She even went on vacation with the family now for three years with all her expense covered. The VanderWoodsen-Bass family were not hurting for money. In fact, she heard Charles Bass, or Chuck exclaimed how much cheap land he was going to buy up now. Apparently her suffering and many others were good for his business. Yet, Blair was able to keep her head held high. She was determined to go to college and enter a career that would restore her family name without retreating to her father. Once upon a time Harold Waldorf was her favorite person in the world but it was many years since she thought that.

September 2004

 _Blair listened to her parent's arguing constantly these days but she now zoned them out. Putting headphones on and sitting down to try to think of ways to oust the juniors who were currently the 'queens' of the school. She was only a freshman but she knew she had what it took to be in charge of the social hierarchy. In fact, she just wished her parents would divorce. P's parents had split and she got two of everything. Blair was already mapping out the two vacations, two Christmases, and two closets she would have in Manhattan. Surely it would not be that bad and could help her status because double closets meant more clothes and the buying of affection. But today was her mother's opening fashion show in New York and they were all to attend. She even managed to get three friends, Serena, Iz and Peneolpe tickets. She only invited Iz and P so they could awe and ah over her mother. As much as she did not get along with her mother she knew her mother' dresses were usually amazing. Eleanor left without them to the show in order to go over last minute details._

 _Once inside with her friends and her father she instantly forgot about all the marital problems her parents were having. She was thirteen young almost fourteen and free on a Friday night. Laughing and gossiping with her friends she never knew the night would turn out as it did. Her mother show was a disaster. The editor and chief of Vogue walked out halfway apparently bored with the designs. Even Blair could see her mother had heavily borrowed on last season and on other designers. Even the quality of the material going out on the runway looked a bit cheap. Angry and wanting to leave and depending on the Waldorf car service to take her and friends home she went in search for her father. Her friends were all with her as they searched backstage. It was chaos but she found someone who told her they saw her father walking toward the sample room where the clothes were housed before the show. So friends in tow she went searched desperate to leave not wanting to hear P's jibs about the show anymore._

 _Opening the door, the young Blair was mortified to come face to face with her father as some male model humped him from behind. Not knowing what more to do them scream. Her friends were stunned into silence. Discovering one's father is gay is shocking to say the least but discovering the person you were closest to in the world keep such a secret was too much to bear. Her scream alerted others and her mother was soon in the room. It was beyond embarrassing when her mother began to speak._

" _Oh, dear you found out your beloved daddy is a homo, Ha! Yes, yes he has screwed every model that has ever worked for me. Certainly now you see why you have no siblings," Eleanor said slurring as she stomped into the room. She was obviously drunk. She began laughing pointing at her husband. "Your zipper is still down dear but there is not much to see there which is probably why your father likes to take it up" Eleanor begin to say but her words were cut off by Blair's embarrassed wretched sob._

 _The tears were already falling down her face by the time Harold who quickly redressed began to apologize. Serena grabbed her best friend and took her out of the room before saying Blair was staying at her house. The damage was done by that point however. So the girls left in a yellow cab. Even Penelope was silent as she held Blair's hand in the cab telling her that it was all going to be okay. As child of divorce she had nothing by sympathy for Blair._

 _The next day Harold begged to speak to Blair. She loved him more than anyone in the world and she would not hold his preference for men against him. She just wanted him to be honest with her._

" _Blair, I am so sorry you had to discover my situation like that," he was clearly uncomfortable._

 _Trying to please her father like any good daddy's girl she hugged him. "I love you and I always will."_

" _I will always love you too. You are the best thing in my life," he told her and Blair happily expected his praise. "I am moving out today."_

" _Oh okay," Blair said a bit stung but understanding that their parents divorce needed to happen._

" _To France. Roman and I have been eyeing a vineyard in the South of France. You can practice your French," he said with a teasing smile._

 _Roman? Her father had a serious boyfriend? They were leaving New York Sure New York city had always been her home but France was chic and she did love the air in Southern France._

" _That sounds lovely daddy. But what about your job?" she asked. He was a lawyer for investment capital company and a damn good one at that._

" _I am retiring. I am in love for the first time in my life and I want to enjoy that before I have a full head of greys," he joked._

" _In love. Really? With Roman? Can I meet him?" Blair asked cautiously. She wanted to meet this so called love of her father's life. Was it was that young model from last night. He was closer in age to her than her father. Surely this was a midlife crisis._

" _Yes. I am so happy you are okay with this. After last night… I am so sorry that you had to see that with your friends..." he trailed off his cheeks reddened with shame. Blair knew the gossip and jabs were going to be tough but she was going to France. Those girls, sans Serena were behind her. New York was behind her._

" _I have some things I need to do but we will talk more okay. We are taking the seven o'clock flight out tonight. Bye Blairbear" he hugged her tightly and peppered the top of her head with kisses. He even cried a bit. She was sure he was happy that she understood his sexual orientation so well._

 _So Blair began to pack quickly. She knew she could not pack everything in a measly two hours but with Dorota's help she packed at least three weeks' worth of clothes figuring the rest could be shipped over. Going over a list of what she wanted to retain and give away with Dorota she then called her best friend to let her know that there was hardly time to say goodbye but she promised her best friend that could come and visit. By five o'clock she waited in the foyer. Her father had left that afternoon and had returned and she was worried. She called him but it went straight to voicemail. Finally, a quarter to six her mother entered the foyer. She looked tired and depressed. Blair felt sorry for her mother. Surely it was not her fault her father was gay. Still her mother callous remarks from last night did still hurt even if she was obviously drunk._

 _With a quick look at Blair's luggage amassed in the foyer Eleanor's eyebrow furrowed._

" _Dear," her voice was even and hesitant. "Are you going somewhere?" she asked._

" _With Daddy to France," Blair answered finally stopping pacing and glancing her cellphone. "The plane leaves at 7. I don't know where Daddy is at."_

" _Blair he is leaving with Roman. You are staying in New York with me," she said cautiously afraid of hurting Blair's feelings._

" _What? No… Daddy said…" she recollected the conversation. He did say we. Certainly he meant Roman, himself and her. He wouldn't leave her. They were close. She did not misunderstand him._

" _But he hasn't even packed," she said. She was home all day and her father took nothing out of the penthouse._

" _He did last night. While the show was ongoing. Movers came in and took his stuff, dear," Eleanor explained as she sat on the steps. Panicked Blair not believing her mother took off running up the steps into her parent's room. She quickly assessed the closet. His side was empty. It was like he was never there._

 _Running back to her mother with a wild look of confusion she needed answer._

" _But he said we. I know he did…. How could he leave me?" she asked with watery eyes. Blair was surprised to find her mother hug her tightly. Blair knew this meant he probably planned this for weeks maybe months to have all this sent up quickly. When did he buy a vineyard she wondered. He planned to skip on her for months probably._

" _He left us Blair," Eleanor said and Blair began to sob._

" _But what did I do. Does he not want me?" the broken girl asked her mother. Eleanor for the first time in a long while put her own hurt aside and let her daughter cry out._

" _Nothing you did. You are the perfect daughter. I love you so very much Blair and I am sorry that me and your father did not obviously handle this correctly. He wanted to talk to you alone and promised to explain everything. I thought he would have but it seems he mislead you or you misunderstood. But Harold has made plenty of promises to me in the past that he easy broke. I hoped he would not make promises to you he never had intended to keep."_

 _Angry and embarrassed that her father left her Blair went to sleep after a long talk with her mother. Blair cried together for the lost of her father. It was the next day mid-afternoon when she finally woke up. She discovered her father had left her a voicemail. It seemed like he was informed of the so called confusion that occurred yesterday._

" _Blair I am sorry that you thought you were coming today. I only met that I hoped you were visit. Roman and I are starting our lives together. I wanted to be free of my past life- not that I mean you are my past life. Of course not dear. I just need some time to be Harry Waldorf the man not the father if that makes any sense. Please call me back."_

 _He wanted to be free of his past life? Well he would never again have to worry about being a father again. Angry her father's voicemail only made her further hurt. Where was the man she idolized? She never picked up a phone call or listened to a voicemail, his gifts were sent back unopened. She was done with him._

 _It was three months later that a carrier came with documents from her mother's lawyer. She knew it was the divorce proceedings. Harold Waldorf had an airtight prenup and was been even stingier with his money since all his communications to Blair were unsuccessful. She knew from her mother that he was taking it out on her but Blair refused to swayed and Eleanor said she was not going to force her. However, Blair would have to understand this meant a tighten budget and certain luxuries were not to be afford. Still Blair held her head high and said her father was dead to her. All she would have of him was the Waldorf trust his father, her grandfather made for her to be opened at 21. It totaled at 15 million dollars. Her love for her beloved grandfather who was now past was the only way she knew she tolerated that money but she could not open it for another 6 years without her father's approval. She knew he would not approved of her opening it to give her mother some so rather the Waldorf women were going to have to do without the Waldorf money for a while but were still going to somehow figure out how to function with the grace and class of a Waldorf women._

 _So the Waldorf women scrimped and saved. They threw less parties and went on no vacations but they still were well respected and admired by the Upper East Siders. Waldorf designs had bounced back after that horrible show and her mother was expanding the business. Money wise things were approving before the recession. But Blair the once hopeless romantic's heart was shattered by her father and what felt like his abandonment. Even Eleanor encourage her to reach out to Harold as Blair grew but Blair steadfastly refused. She even went as fear to lock herself in her bathroom when he came to New York to surprise her for her 16_ _th_ _birthday. Crying out behind her locked door she begged her mother to send him away. Harold hearing for himself the pain he brought to his daughter finally stopped attempting to reach out. The ocean between them grew as the time past._

So when Blair turned 18 in her senior year at Constance she thought all was well in the world. She was accepted to Columbia University early decision having washed herself of her father's dreams of Yale. Serena and her were determined to enjoy the rest of their senior year. The recession had tricked down into their lives of their friends but Blair was not ready to find her mother, who she was incredibly close to at this point in tears one day after school. In was the beginning of January. People were still wishing each other Happy New Year but Blair's vision at 2009 being special came crashing down that day.

"Mom?" she asked concerned. It had been four years since the divorce and her mother had not been this sad since then.

"Blair everything is gone. They are going to seized the penthouse," her mother sobbed. Looking at the table she saw all the paperwork, excel sheets, and figures on her mother's laptop that was piled up before her mother. "I was keeping it from you but it is to the point where I don't know what to do anymore."

Eleanor explained how much of their saving were taken away by a Ponzi scheme on Wall street, and recession had lowered the value of stock in Waldorf Designs, and it was such a bad time for the male line expansion. Blair knew they have the lavish account some of her friends did the past four years but she did not need for much. She still brought high end clothes less of it and with Serena's help Blair was still one of the most stylish and fashionable girls in Constance. She needed to be as Queen. Before unused clothing would just sit in her closet now Blair only purchase clothing were they really suited her or for an occasion. They still ate out on occasion but they had to let go of the other full time maid and cook but they still had Dorota. But she never expected her home to be taken from her. Feeling faintish she took a seat.

"You can use my college fund. I will defer for a year. By time we will have this sorted. And I can apply for scholarship and stuff for the difference," Blair said.

"Blair," he mother said taking her hand. "They already seized your college savings and we had the tuition for your freshman year transferred over to my account to begin paying for your expenses. My lawyers are fighting with the bank now to stop them from taking the rest of it."

"But… how did this happened?" Blair asked confusion.

"I borrowed against the penthouse to Men by Waldrof Designs last year. Since that failed and there was no revenue I can't pay off the loan. The savings are gone because of the pronzi scheme and the stocks we had are devalued and taking them out now would be a loss," she explained to her daughter. "Without 20,000 by the end of the month the bank is coming in and valuing our processions to be sold at auction."

Twenty thousand dollar surely her mother had jewelry she could trade in valued that high. "Mom what about your wedding ring?" Blair asked hesitantly. Her mother never wore it but it was still a sore subject.

"Its gone, a few months ago. I already sold it. I was able to keep the creditors at bay for two months with it. And I wanted you to have a good Christmas."

Shocked that this was occurring for so long Blair was once again feeling hurt by her parent lack of trust in her. Why did they always hide things from her? She was capable, wasn't she?

"I need to go," Blair mumbled as she stumbled out of the room her breathing became harder.

She walked out to the elevator clutching her last season Chanel handbag wrapping the Marc Jacobs coat that was one of her Christmas gift tighter around her. She supposed if they lost the house at least the Jacobs coat would keep her warm.

* * *

Let me know what you think of the story. No Chuck yet. We will met him in the next chapter. I needed to set the stage for the reason why Blair is broke.

Also, this I think the most dramatic story I have written as of yet. A lot of twist and turns will occur. ;)

Please review.


	2. Around the Corner

A.N: Thank you for all the warm reviews so far. They mean the world to me. I am not sure if this chapter is perfectly what I want it to be. I am still struggling with writing in the third person format.

To the reviewer who pointed out the similarities between this story and another call in "In Love and War" thanks for the call on that one. I had a chance to read the first two chapters and summary and it seems like that story is set in a dystopian future plus a marriage of convenience plot. So far they don't really seem that similar since my story is set in the recession that actually took place in 2008. Plus, another reason that will be touched on in greater detail is going to be the aftermath of the 2008 presidential election which opened up a Senate seat in New York and that was replaced but which caused in opening in the local NY politics. The political story line is centered around Nate and his family that is going to be affected in a way because of the Chuck/Blair deal. The title is similar and of course an economic crisis but beyond that hopefully the similarities end. I really would not want a completely unoriginal story. But let me know what you think and if the similarities continue.

* * *

Chapter Two- Around the Corner

Happy to have the holidays behind him Charles could finally enjoy his favorite pastime again. Women. He found if he spent the holiday casually having sex with a woman he risked them having the misconception that there would be a gift involved or some sort of feelings on his part. Plus, he did love spending the time with his family. It was the one time of year that he was not completely focused on work or women and could enjoy feeling like he belonged with his step family. New Year's he threw the biggest party and got right back into his favorite physical activity. A few days back in the game he had already had a blonde, a brunette, two red hairs, a girl with purple or was it blue hair later he was finally feeling energized from all the activity and was wishing everyone he saw a happy new year.

No doubt, the man loved women. Tall women, short women, women with curves and without, straight hair, curly hair, wavy hair, natural hair, fake hair, were all enjoyed by Charles. He loved women and while not religious always remembered to thank God for women whenever he was inside one usually while they were calling out to God themselves. He found women soft, strong, perfectly shaped Venuses that he worshiped. The only problem was he could never remember their names. The numbers he had in a black book with physical depictions and a rating of the encounter. Yes, some may consider him a douche, slut, whore, a pig, a womanizer, an ass, which of course he was but he never cared. He found in the arms of women what he could never find elsewhere. In the moments when he achieved his own sexual gratifications he found peace. A solace that was never there otherwise. Day to day there was always something more he needed something just around the corner it seemed that would never come. It felt so close in his dreams he almost knew what it was. However, at the moment he did not quite know what he was searching for. So he kept searching for it in the women he took to bed but to no success.

Another person rushing in a city of millions ignoring the world around her. The cold wind on a bright day, dirty slush that was once white snow wet the streets that Blair walked over. The whole New Year feeling was already feeling old and dirty to her. But she only had one location in mind. The van der Woodsen siblings and Lily lived in the Milan Condominium Building on 300 East 55th Street. It was in midtown and far from Blair's Upper East Side home but she walked in the cold her brain trying to remember if there were any signs that this was going to occur. Was there anyway she should have known. Her hands, with no gloves since she forgot hers in the foyer were cold and were beginning to feel dry and turn red. Her hands were tucked into her pockets but her face was unprotected and she knew her cheeks and nose were red. But her eyes were shining with determination and fear. Blair knew she had to figure this out. She walked on needed the fresh air to soothe and keep her tears at bay. The would never break down in public so she continued on stomping her way over the concrete jungle until she got to Serena's trying to formulate a plan. Nothing came to mind. Money did not grow on trees regardless even if it did she was a city girl. What was she going to do with a tree?

She hardly noticed that Charles Bass was behind her. Chuck as he was known to only his family and very close friends was a notorious playboy of the New York. He was almost five years her senior and for as long as Blair could remember she had a crush on him. For most of their life she hardly thought he looked at her. While hardly any of the polite UES society wanted nothing to do with him Blair knew he was not a bad man. She saw the ways in which he cared for his family and took over the large company after his father died. After joining their family vacations, a couple of years ago she was able to discover a sweeter and funnier side to the mysterious man which only served to increase her dreams of him. She admired him from afar never hanging on his every word or off his arm like she had seen so many women do.

Charles Bass was a mystery to not only New York but quite frankly to the whole world. After his father's passing at sixteen he continued to be educated at a boarding school for young men away from the city but technically remained a legal child of his step-mother Lillian Van der Bass nee Woodsen Rhodes. The business world was shocked when at eighteen after high school rather than only attend college decided to both attend school and begin to transition to take over the company, his birthright. The Bass board protested violently and the Bass Inc. stock dropped at the thought of a child controlling one of the largest American companies. Chuck received calls from prominent business men, politicians, and even opinion articles were written against it. He ignored them all and somehow received enough voice of confidence largely supported by Lily and a few other stock holders in allowing him to start the transition process. Within eighteen months he stunned the world with shocking deals and crazy investment ideas but somehow they almost all panned out. He was regarded as a business men of the times and was winning award after award all the while taking classes at Columbia. The school in a rare moment decided to award him a bachelor's degree in business only after two years citing his hands on experience and two years later he was close to receiving his masters. Yet, it annoyed him to no end that his stock market value of BI had not gone up in the way that it would have had he been a mature adult who did not have his eccentric lifestyle. Now with the market being the way it was he was worried the gains that he made were never going to truly reflect the true success he achieved. Even still as banks were halting lending money across the board they were still handle him multimillion dollar loans as he began projects in Brazil and Panama.

Besides being an extraordinary business man all the world seemed to know what that Charles loved women. The local media likened him to Bruce Wayne the playboy persona who was also Batman. Articles ran in magazine wondering when Charles would be unmasked and dozens of reporters attempt to find the edge in discovering who was the real 'BassMan'. Yet, no one really saw anything beyond the clubs, the drinking, and the women. The only other question people had was when did the man sleep? He was photographed in Bali on a Saturday night and suddenly was in China on Sunday in meetings. Conspiracy theorist even claimed he certainly had a plane that could travel at the speed of light adding that the press called his Bass Mobile.

But to the van der Woodsen's he was just Chuck. So, Chuck on his way over to drop his dog, Monkey over to his brother Eric for the weekend. He turned the corner and saw Blair walking into the building. He was happy to see Blair Waldorf still in the elevator and held it for him once she saw him in the lobby. They were the only two in the elevator since Lily's more modern building did without a liftman. He knew the Blair for as long as he knew Serena and he enjoyed her company far more than he knew he should. Around the time she turned seventeen he was shocked and angry with himself to find that he had developed at some point a desire for her. For so long his party life and his family life were separate. He was aware she had a crush on him for years but had thought nothing of it than a school girl crush. In his mind he thought the protectiveness he felt for her was similar to a sibling relationship but that was not so. Yet after the family vacation to St. Lucia the past summer he found the tension too much to bear but she was seventeen and he distanced himself from her. But now he knew she was eighteen. He sent her flowers every birthday or at least she was on some list that reminded his assistant to. Did he send her a Christmas gift, he wondered? Hopeful that would grant him some of her favor especially in light of his quest to have sex with her. The billionaire never knew a woman who did not eventually fall for his charms he was sure that she would be no different. He was sure she was mature enough to not cause problems with Serena or Lily so the charm was on full display for her.

Summer 2008

 _The family usually took a month vacation and Chuck joined them his last two weeks. This year he brought along Nathaniel who was two years younger but had went to high school with and then Nate followed Chuck to college at Columbia. The two had bonded over the death of Bart Bass one night at high school and ever since Chuck truly valued his friendship with the man. While the two could not be more different they were fiercely loyal to each other. The only thing they seemed to have in common was sleeping around with women._

 _They had planned to do plenty of women chasing in St. Lucia when they were not engaging in the 'family activities' that Lily had planned such as jet skiing, underwater deep sea diving and snorkeling. It was on one of those days that Chuck was shocked to see Blair in a brunt orange bikini that looked amazing with her new tan that made Chuck hope the water was going to be cold._

 _Nate already warned that Serena was off limits to him leaned into Chuck whispering "Bro, she is not your sister right," while looking at Chuck._

 _Chuck who was very much looking at Blair in a not so brotherly way turned to his best friend saying "She is off limits Nathaniel."_

 _The venom in his voice was unmistakable to Nate. He instantly knew Blair was different to his friend. But he knew better than to push the point. So instead he made sure that his eyes never rested too long on the brunette because he was fearful of Chuck's attitude. So the boys surround themselves with local beauties instead on the trip. But there was one night, one of the last nights on the island when that all came tumbling down. The four-some were out clubbing when suddenly the joyous night took a turn for the worse._

"Happy New Year kid," he greeted with a dashing smile falling back on an old nickname he would use for her.

"Hey," she said never sure if she should call him Chuck, Charles, or Mr. Bass. So she stuck to simple greetings.

She was in awe of his persona and his person. She knew a bit of the man behind the myth and while intriguing it was his looks alone that had him sneaking in her dreams in the darkness of the night. He had brown hair that when he grew out had a slight wave to it the Blair always wanted to touch. His rich brown eyes that when he stared to too long at her made her blush. His eyes were under dark rich heavy eyebrows made him look terrifying whenever he was mad. Oh, and when he was mad his jaw would tighten into a strong line that made Blair's stomach tingle. His pink perfect lips edged out in the cutest of ways when he was stern and businesslike that reminded her of his late father. But his smirk was completely uniquely Charles Bass. But she did never fall to his feet the way Serena's other friends did. She used to ignore him only because she did not want to melt at his feet. As she got older however, they began to tease each other until they got to this full on flirty banter that they currently shared. However, sometimes like today when she had no expectation of seeing him he made her embarrassed at the thoughts in her head.

Blair was not the most beautiful women he met nor was she the most graceful, tallest, or petite. Yet, he always looked twice, trice, hell twenty times at her. There was something there. Maybe it was because when she smiled he smiled or because even when she frowned she still amazingly breathtaking. Or maybe it was because it was the way she looked at him with big brown eyes that screamed I adore you. Did she idolize who he really was? No, he thought, no one knew who he was neither did he. Even still it made him feel good about himself. He may not like who he saw in the mirror every morning but he liked who he saw in Blair's eyes. He wondered often how it would feel to have her look at him that way when they had sex. Which of course, in his mind they would someday. It was inevitable. She wanted him more than she even realized, he could tell. He wanted her too. Her porcelain skin that he was dying to touch, her straight wonderfully angled nose that wanted to run his finger down to her perfectly indented cupid's bow. God how he wanted to kiss her full lips.

She unbuttoned her coat to escape the rush of heat that hit her in the elevator after being in the cold for so long. Underneath she still wore her school uniform. He was surprised they were back in school already after the winter break. Her white button down shirt had the top buttons undone with her tie gone. When she leaned down to pet Monkey as she said her hellos to the dog. There is no doubt that having a dog is a chick magnet. Not only do women stop to pet his mutt they also always bent over giving him a wonderful view of their behind or down their shirts. This time was no exception as he took in Blair's white lace bra. She had no clue.

"I am bringing him over to stay with Eric," he informed her to fill the silence in the elevator. She normally was never this quiet. Pausing her petting she looked up at him realizing his gaze she shot up and blushed. He only smirked further causing her to roll her eyes.

Blair knew she was playing with fire the way Chuck and her had begun to flirt the past few months but it had never moved beyond that. She doubted that it will. She thought it was his nature to flirt that he never took it seriously. She would have loved for more but he doubted if he could ever give her what she wanted and she would never let a man close enough to earn her trust. After her father's betrayal she found it difficult to not only date but to even make new friends constantly afraid that people's love was fleetingly. The only person she really still let into her life was Serena. So she understood the need to keep people arm's distance away never having real conversations so she enjoyed the pointless banter that now existed between the two of them.

"Where are you going?" she asked as the elevator opened to the top floor.

"Aspen, a short weekend," he said with a wicked look in his eye that left no doubt in her mind that the only slopes he was interested in this weekend were surely on a woman's body.

"New girlfriend?" she said asked playfully smugly.

"Never. I quake in fear at the thought of having one," he said fulling serious but with teasing eyes.

"Oh course. Why settle for one women when you can sample them all," she said hoping the jealousy in her voice was not clear to him. She was unsure if she wanted to be another notch on his head board but she definitely wanted to appeal to him the way he did with her.

Laughing he said "Yes well some women are well valued over others." He was flirting and he only hoped she could recognize it.

"This girl from Aspen must be a very high price to spend the weekend with you," she said a flash of anger in her eyes that he could not understand. Unless it was jealously. This time he saw through her mask.

Taking his chance, he moved closer brushing a hair from her face. "I could always trade her in for you."

There was nothing teasing or sarcastic about his words. Instantly he knew he meant them and her stomach twisted and she suddenly felt hot. For a moment she thought of saying yes and letting him have his way with her. Surely she would be satisfied by him. But she had other things to think about maybe when she was poor she would let him whisk her away a sex filled weekend. Plus, she was not an item to be traded.

Backing up slowly she said "No thanks. But try not to dream of me when you lay next to her." The small smile on her face put them squarely back into their light teasing relationship that she was used to. Chuck smiled at her clever response. Eric came from his room and greet them both. Blair walked her way to Serena's room never glancing back. She thought of mother and her problems trying to force the thoughts of Chuck out of her mind.

He wondered if he took it too far too soon. A girl like Blair would need months of wooing.

Instantly Serena knew there was something wrong with her best friend since she showed her unannounced. Within moments Blair confessed all the problem her mother had mentioned today to her best friend. Serena and Blair were inseparable from the age of three and they had never not shared everything with each other. As close as sisters they fought as hard too but no matter what the two girls never let anything or anyone get in between their friendship for too long.

"So the mess with the line, the recession and the failing stocks, the Ponzi scheme, and your college fund might be gone," Serena summed using her fingers up once Blair had relayed the story.

Blair nodded wiping away a stray tear.

"Oh Blair don't cry we will figure this out. I am sure your mother's lawyers are working on it," the hopeful blonde encouraged.

"No. No. it's so bad. My mom sold her wedding ring to pay the bills for the past two months and for Christmas," mortified Blair hung her head in shame.

"Wow," Serena gasp finally understanding the full effect of the situation.

"That's not the worse part," Blair said as the full tears came running down her face. "they are taking the penthouse if we don't pay 20,000 owed. Even that would only hold the creditors off for a time. I think we have like five days," she mumbled.

"Blair maybe I can ask Chuck or my mom to lend me the money from my trust," Serena said willing to do anything for her best friend.

"I cannot ask you do that. You already do too much," Blair said as she wiped the tears from her eyes. There was only so much charity her pride could handle.

"Why not call your dad and ask him to open up the trust your grandfather left you?" Serena asked knowing the answer well.

"I am not asking that man for nothing. Nothing at all. I don't need him," Blair said with anger her sadness slipping away in an instant.

Unknown to the two women Chuck stood in the hallway listening carefully to Blair's sad tale. He had encouraged Eric to take Monkey for a walk and made up a lie about wanting to see Lily who was napping in her bedroom. He never lied to his brother before but he was eager to hear the conversation. He thought perhaps Blair would mention his advances to Serena and wondering how she thought about him. Instead he listened to her tears over her money situation. Money was something he had plenty of. Suddenly getting into Blair's pants seemed like child's play.

Blair excused herself to grab a bottle of water and wash her face. Understanding her friend needed a moment alone Serena stood in her room. She was surprised to find Chuck standing in the kitchen sipping a bottle of water himself alone. Not in the mood to be pleasant she said nothing to him as she opened the fridge to grab a bottle for herself and Serena. She could feel his eyes roaming over her. She knew her eyes gave away the fact that he was crying only moments earlier but she refused to blush under his gaze.

"I can help you with your problem," he said stopping her. She looked over at him finally.

He was leaning against the counter his elbow propped up on the island behind him with his feet crossed over each other. Her eyes drifted over his body from his navy pinstripe suit to his pink pocket square and matching pink and navy argyle socks with patent black closed laced shows that had pink side stitching that was so subtle she would have missed it if not for the lighting. He was in the center under the pendent light and where she stood shadows casted onto her face from the beamed she stood by.

"Yea and what problem is that?" she asked with some apprehension. Perhaps he overheard her conversation with Serena and would lend her the money.

"The money problem," he said. Her eyes blighting at the thought. She always thought the best of him. He was such a good brother and son and now he was an amazing friend. Yes, she would think him her friend after this.

Borrowing again and again from Serena was too much but she knew that Chuck would allow her and understand that she would want a loan not a gift. She would ask for it in writing and that she would want to pay him back as soon as she could. Handle this like a business arrangement made her feel older and more confident. She stood straighter.

"Oh that is amazing. I am not sure," she began to say but he silenced her when he placed a finger to his lips with a gentle shh. Suddenly a lecherous smile appeared on his face. This was not him being kind. No this was him being cruel.

"One night twenty thousand," he said. Chuck knew they would end of in bed one day from her looks and their flirting. This way it was easier and she got something out of it at least he figured.

Blair blinked away the tears she felt. Chuck was the first boy she ever had a crush, she thought herself in love with him when she was young and silly. He saved her once from a terrible situation and she felt forever grateful to him. But now she thought he was as horrible as everyone said he was.

Taking a deep breath, she thought of asking him for a loan. Begging him perhaps through Lily. Or maybe just walking out of room and anyway from his money. But then what Blair, she questioned herself, walk out right into a guest room at a friend's or right onto the street? But in five days she needed the money and she was tired of Serena and Lily's pity to her. She decided to approached this as a business deal. Women have done this for centuries, she thought. Sex for money. Her body for a night. Viewing the deal as separate from her feelings she began to consider it.

"Fifty," she said bartering hopping she looked more confident than she felt.

He smiled at her negotiation. He chuckled and she felt like throwing up but kept a stern face.

He had very clear rules for one night stands. Women were never to stay the night with him if it could be avoided. So he surprised himself when he said "For a night, the whole night. That means dinner, dessert, and breakfast the next day I'll make it sixty." Really he wanted to ask her to come with him to Aspen but two nights might be pushing it.

In Blair's mind that meant potentially helping for mother for 3 months. She could not be that selfish. If she would have agreed to visitation from her father, they would have had child support and they would not be in this mess. Where would they even live if they got kicked out?

Nodding she stuck out her hand to shake with him. "One whole night," she said.

"Sunday," he said to her taking her hand. He restrained himself to only a handshake knowing he would have so much more than in three days' time.

A.N: I hope I was able to convey the sense of the character I am trying to build up here. I want Chuck to come off edgier and more sure of himself since he is older. He is not supposed to be nice or understanding at this point but for anyone turned off my this his character will of course develop as he begins to have feelings for Blair. Blair, is young and very turned on by Chuck. She has a crush on him but I would not classify that as anything more. She does not really know more than his persona truly but the parts of him she does know she does genuinely admire and respect. Chuck likes that she looks him in that way but doesn't get that buying sex from her does not mean she going to continue to admire him. These two characters are not in love and do not really have feelings for each other besides lust at this point which is different than I have ever opened a story for them. I hoped I conveyed that.

The title of the story For Love or Money, as you might expect by now, will apply to multiple storylines in this fic. There is more than one subplot with Chuck and Blair romance anchoring the rest of the story. I anticipating this to be my longest story with many chapters - spanning from January 2009 to May/June 2009. I hope the twist and turns keep you entertained.

I hope every recognizes the chapter title and its significance. "Day to day there was always something more he needed something just around the corner it seemed that would never come." And then he sees Blair walk around the corner into the building.


	3. The Candidate in the Mirror

A.N: The response to this story has been amazing. So thank you to everyone who reviewed. I hope everyone enjoys this new chapter.

To the reviewer Lucy who said this reminded them of Indent Proposal I shamefully admit I have never saw the movie. But once I saw the review I looked up the trailer on Youtube and I have placed it on my to watch list. I love vintage Demi and I so angry that I have never seen it. It looks amazing. I love spoiling the ending for myself and I saw the final scene. It was amazing. So thank you for alerting me to the movie.

Maureen Van der Bilt is make her first appearance and she is OC. Her character will grow to be more like that of the show. It is just essential that she appears very upset and not cool and calm as she faces the scandal. The special election seat is opened up after Clinton left her Senate Sate to be Sec. of State and then the State Senate open up after Kristen G. ran was appointed to that seat. The was over by Feb but I will extend that out for the story.

* * *

 **The Candidate in the Mirror**

It was dark and cold outside. It seemed like the city was still sleeping but Charles was up and alert never comfortable sleeping the whole night besides a woman. He got out of bed naked walked over to his trousers and slipped on his pants. Not concerned with making noise he simply ruffled through the clothes in the closet the maid had packed earlier to find a clean shirt. He was button it up when the women in his bed stirred.

"Mmmm where are you going? Come back to bed," she said in a sleepy voice she no doubt thought was seductive.

Frankly Chuck was more than annoyed with her and this whole day. So he said nothing as he flipped the light on in order to put on his shoes. Her comfort be dammed. He felt the bed shift as she came up behind him rolling her hands over his shoulders.

"I did not tire you out it seems," she giggled as she moved down to bit his ear. He pushed away and bent down once more to tie his other loafer.

"Its fine. I need a drink. You sleep," he said briskly as he rose and put on his watch and grabbed his wallet.

He did not look back at her but instead opened his wallet to find it missing a few hundred missing. Glancing up at his bedmate he noticed she was looking away and her body was tense. Chuck of course had this occur numerous times to him whether it be working girls or seemingly sweet ones. Once the women realized that she was not going to get anything more than a good dinner or a short trips with him they were always quick to pocket a few bills. He was no one sugar daddy or sponsor. He liked sex not a keeping a women dressed to the nines with diamonds and jewels. Rolling his eyes he took a deep breath.

"As long as you know better than to swipe a card I really don't give a fuck," he said to the women in his bed. She looked up at him her eyes fearful and biting her lip.

"What… what are you talking about?" she asked.

Chuck smirked and moved back to the bed. He twirled a lock of the model's hair. She was on the model scene and while beautiful had a drug habit that stopped her from breaking out into the top world of modeling. He thought it would be fun to ski and she told him she loved to ski. Chuck was annoyed that when they went earlier that day to ski she did not know anything. So he left her behind as she struggled and he flew away enjoying the rush that he felt when he skied. She was not going to hold him back.

"You know girls like you pretend that they are above whores. You want someone to give you money and pay for nice things and yet you act like you are better than the women who work the street but you are playing the same game. Frankly, I don't care if I have to pay you as long as we are clear about the deal. So tell me is this sex for money or sex for pleasure. If it's the former you can keep the five hundred," he said challenging her with a cruel smile on his face as he tugged on the sheet exposing her body.

He did it on purpose made her feel cheap because he felt the same. The deal with Blair was messing with his mind and his emotions. Here he was complaining about a few hundred in cash. He just wanted to be worth more than his body or his wallet. It was the reason he could not sleep. She teared up and pointed her chin at him. Looking away from him at the wall she then said "Would you give me more if I say it was for money?" she asked. She seemed to have never been so directly asked in this matter and the shame was on her face. But she decided to milk this ass whole for all he was worth.

Standing up Chuck tossed the rest of his cash probably four hundred dollars onto the bed and said nothing. He was going to walk but stopped pausing at the door of the bedroom.

"I'll make sure you have a flight to leave Aspen. Where would you like to go," he asked half out of mercy and half because he did not want to take a flight home with her.

"Can you book one to Los Angeles," she said her eyes flashing back to him a tight smile on her face pretending things were back to normal. He nodded and walked out wondering how long the cash would last her with her taste and her drug habit. Shooting a text to his assistant and giving him the number of the room he told him to call and figure out the flight details.

He made his way down to the bar. They were staying in luxury hotel cabin that housed a few rooms but was spacious and gave you that ski lodge feel with a modern twist. Walking into the dark wooden bar that was opened 24 hours he noticed it was empty. The only sound coming lightly from a news channel that the bartender was watching.

"Scotch, neat. The best you have," he said as he sat down gaining the bartender's attention. He was a middle age man in his late fifties who loved working the late shift. The hotel paid him a salary over tips since he manned the bar with little customer but they wanted to keep the option open for guest. He got paid god for little work and when guest came in they would tip unbelievably well on top of it. After all the years on the job he could always tell when a patron wanted company or silence. This man clearly wanted to be alone.

'Breaking News' flashed over the television drawing Chuck's attention upwards.

The bartender placed the drink in front of him. "Want me to mute it?" he asked recognizing that Charles was a man who liked silence.

"New York politician disgraced is the leading headline today out of New York City and we are going live to the Van der Bilt mansion with Brenda Cormack for the latest. Brenda," the women anchor began.

"No. Higher the volume," he said interested as he sat up straighter watching the news.

"I am standing here in front of the Van der Bilt compound located about twenty minutes from the city. We have reports that a large part of the Van der Bilt clan is hold up in a makeshift war room discussing how to react to the revelation that occurred overnight in which photos of William Van der Bilt the 3rd also known as Tripp who is running to fill Senator Gillib- State Senate seat in this special election cycle. Photos of the Van der Bilt surfaced on the web last night and outlets in California broke the story around midnight Pacific time making it only four in the morning on the East Coast. It is now seven and we are expecting any moment for a press statement from the family. We can only imagine the last night rousing it took to get everyone out of bed and to wake the lawyers. I believe we have footage you can roll of some of the family arriving here at 3am, 4am and even some moments ago at 6am. We have not seen Tripp enter the house but we can assume he is there. This is surely going to a black mark on this important New York political family.

The photos that are too graphic for us to air on television are of Mr. Van der Bilt engaging in texting explicit photo with various women from New York and there are even reports that one of the women might be underage. It is even reported that he sent a video of himself and his wife engaging in a sexual activity to some women who goes by LuciousXOXOLips87690 on twitter. There is no doubt going to be consequences for this. Mr. Van der Bilt was up in the polls by 25 points so now we have to see the fallout that- What. I am being told that the family's lawyer is walking out of the house. Tripp Van der Bilt is not with him nor is Maureen Van der Bilt. There yes can you see him. Okay he is walking over now to where the press core is located. No doubt, he will have a statement for us."

He sat in the family living room watching the live coverage as Stan Hackberry was reading the statement that was put out my family. He said the usually the family is going through a hard time and blah blah blah plus more lies. The truth was the family was livid and probably wanted nothing to do with Trip. Nate groaned covering his eyes to peek out from behind his eyes and the statement was over and the reporters began shouting out questions. Press conferences like this when the lawyer took no question were always a good time to hear what the questions will be when there was a Q and A. In went the usual why did he do this, how do you think the voters will feel, how does his wife feel, etc. But the question that perked Nate to sit up and look around the room was the question 'Is cheating a Van der Bilt trait.' He glanced over at this grandfather who stood by the window sulking, thinking, carefully planning his next steps.

The Vanderbilt family was one of the oldest in the city and even American. Through the last couple of years, the skeletons in our closets were plenty and destroyed the family name. William Van der Bilt the family patriarch was once governor but had to resign due a secretary in his office who outed him for sexual harassment. He was not arrested and destroyed the women in the media. Angela Pinckney had no chance in the late seventies of standing up to such a powerful man. Her reputation was destroyed and she was victim shamed in the media. Women in Albany to this day warn other women before filing a harassment claim that they may be the next Pinckney. William's son were all lackluster in the family business including Tripp's father. They were all womanizers who never appeared sincere and never made it beyond the state senate house. William was sure Tripp could be governor one day but that all seemed now like a silly dream.

Nate watched as Trip paced the room biting his fingernails. William was still by the window while Trip's father William the Second was already two sheets to the wind and still going strong with the whiskey. Nate's other uncle Felix was sitting bored on his phone probably on some gambling site. The Captain Nate's father was sleeping in the corner unconcern with his in-law problems by this point. He only came because Ann demand that they all show up around five this morning. This was undoubtedly a space for the men in the family but not a single one of them rose to the occasion to take charge.

Just then Maureen came the doorway rolling two Louis pieces of luggage. Sunglasses over her eyes and large fur coat draped over her shoulders. She was leaving and apparently at this moment. Tripp rushed over to her.

"Where are you going? You have to stay," Tripp begged. Felix nudged the Captain as if to say you are not going to want to miss this.

"I am not staying. Not when there is a video of me online having sex with you. Are you a fucking idiot!" she yelled letting her anger be released. Nate wanted to be swallowed whole. William winced at the reminder.

"We can get through this. The First Family got through this," he reminded her.

"There was not a picture of his penis on the internet! Or a video with her moaning for more," she said her cheeks red with fire. Just then Stan the lawyer walked into the hallway in the study standing awkwardly behind Maureen.

Then Maureen attacked Tripp. The coat flew the floor and her luggage to the ground as she scratched at his face and slapped him. Tripp then tried to back up but Maureen followed him filled with fury. Stan tried grabbing her off his client making Maureen yell further. The only male to get up in the room was Nate as he stood awkwardly unsure how to stop this.

"Enough!" A voice yelled stopping all the commotion in the room. Just like that everything stopped. Anne Archibald nee Van der Bilt stood now at the other doorway in the room her eyes filled with fire.

Maureen backed away from her husband and slapped Stan back. "My fur you slob," she hissed as she pulled him off her white mink fur coat. She slumped to the ground and began to cry as she petted the floor. No one in the room knew if she was crying for the fur or for her marriage.

"Felix get off your phone unless you are doing something to help the situation. Willaim stop drinking. Stan call the networks we need a primetime interview spot now. Captain call the campaign manager we need to know if we can trace this leak. Daddy it's time to start paying people off we cannot have anyone go to the media at this point. All the stories need to be bought at this point. Nate go over with your cousin and make a list of all the other people that could come out and what images and pics. We need control over this by controlling the narrative. Maureen get off the floor. Come with me now. We can fix this and we will. You need to pick the right outfit for the interview. As soon as you are done with Nate Tripp come find us we need to do interview prep." Anne sounded off her commands like a general leading her troops. The men quickly fell in line. Maureen got up slowly pulling the sunglasses off her face. Tears were in her eyes.

Nate felt sorry for her and looked away. This was not easy. Belonging to this family was never easy. It took nerves of steel and Maureen was fragile. He looked at his cousin realizing the scratch marks needed to disappear before the interview or he was going to have to wear a turtleneck. No doubt we were going to need a makeup artist. But for now he just urged his cousin of the room to the bathroom in search of some rubbing alcohol. For a brief moment Nate thought how ironic it would be if Tripp died of an infection caused by a women scorned.

The city was obsessed it seemed with the newest political sex scandal. There is something about sex and politics that just gets everybody interested. God forbid we ever find out they actually had sex. It's like one would think that their babies come prepackaged in Barbie boxes. Everywhere Blair went that day running errands she heard of the Van der Bilt family. Every TV channel seemed to be airing the interview with Maureen and Tripp who looked very much boring family home types in a chic way with his maroon turtleneck and her in her cable knit cardigan. She knew Nate from the Van der Woodsen family vacation but not enough to text him that she was sorry for what his family was having to go through. She remembered well the response to her father's departure. Every time she thought of Nate however she quickly thought back to Chuck and their planned meeting for tonight.

Telling no one not even Serena of her appointment with Chuck today she told herself it was only one night and it would mean very little to her. Riding the elevator up to his penthouse in the Empire she knew it was a lie. Her legs were quaking in anticipation and in fear. She told herself that they were to have dinner first which would calm her knew but she fears sitting across from him and his stares would only make her more nervous. His reputation was legendary and she told herself it was be amazing. Women would throw themselves for nothing at him and she was gaining so much. She knew the sixty thousand would only be a band aid to the problem but it was a big band aid and she figured it would buy time for her mother to settle things.

Entering the penthouse, she heard the sweet jazz melody drifting in the air, the smell of a mouth-watering steak so rich she could almost taste it, and saw the dim room with a table for two set. Suddenly she felt Chuck next to her removing her coat and brushing away the light snow that had fallen on her hair. Leaning in once from behind her more he kissed her neck and smelled deeply the Dior she had misted on herself earlier.

"You smell divine," he whispered as he ran his arms over shoulders and down until he holding both her hands leaving a trail of goosebumps in their place until he took the night bag she had brought with her and placed it down at the door.

Though it was a cold January night Blair knew his home would be warm so she wore a royal blue silk dress that was barely even there. The material was so thin that one could mistake it was lingerie but it loosens to a flare dress falling beautifully over her hips. It was a Waldorf original and she wore it well. The straps were only just enough to hold the dress up. Chuck brought his back to her shoulder under the straps and began to toy with them.

"We might just have to skip dinner," he mumbled as he began to kiss her neck this time with bites and nibbles.

"Chuck," she gasped as he pulled her further back and she finally felt what she was doing to him.

Stopping them Chuck backed away from her. All his conquests called him Charles even a few he enjoyed called him Mr. Bass. He never had a women call him Chuck. It was his family nickname. He thought of correcting her but did not. Like the rule about spending the night he quickly got ride of this one away as well.

"We should eat. It would be a waste to let such fine meat go cold," he said breaking the spell he had over her.

Blair blushed. She thought herself a bit weak for so easily falling into his hands. All it took were a few kisses and she was putty in his hands. There was no doubt in her mind that Chuck would be satisfying her tonight.

When they sat down for dinner Chuck had intend to tease her the whole night. He wanted her squirming under his gaze and fully intended to begin their sexual night with no real true conversation. Yet, he asked about her mother and truly wanted to know more about what was happening. At first, Blair ignored him and tried to tease her way back to sexual innuendos. Yet, Chuck was adamant about discovering the state of her mother's financial affairs.

"She was involved with that Ponzi scheming ass?" Chuck asked shocked when Blair began explaining the situation. He knew dozens of peoples who were tricked by that man. They were never going to see that money again. He felt concern for Blair's future wash over him. He knew her well enough to know she was brilliant and did not deserve this.

Blair nodded as he sipped the white wine. Chuck said she should had had the red but she refused she preferred the sweetness of the white.

"Yes and the creditors took my first year college fund," she said the sadness seeping into her eyes. "So I will probably just take the first year off and try some scholarships or something." She shrugged it off but it was obvious to him that she was hurting.

Before he realized what he was doing he was mentally resolving to help the Waldorf with their lenders more than just the money he was giving Blair tonight.

"I will have my lawyers contact your mother tomorrow. She should fire the ones she has. I'll have my top legal representative Cyrus Rose give her a call," he said full of the usual fire that went with overseeing a billion-dollar empire.

"Chuck, I could hardly accept that" she began to say but he quickly cut her off.

"Yes you can. How would you explain the sixty grand? Probably told your mother it was a loan or something. So say this goes along with that," he explained. He was determined to have his way she could tell so she nodded rather than argue.

"I am not looking for charity, Chuck. I am tired of accepting your sister and your mother's generosity. It's just my father left my mother with no money so it's been hard the past couple of years and now this is just too much," she admitted her defeat. She never thought she would share that with him not when he offered her tonight but it came out so easily it could not be help.

"He doesn't even give your mother child support?" Chuck asked in disbelief. That seemed unfair to him.

"I begged my mother not to allow it because I did not want to see him after he left. It's my selfishness that put us here." she admitted.

"Hardly Blair. You were hurt. I remember when that all happened. Everyone was talking about your father and I always thought your mother handled it quite well after her horrible fashion line. You were just a teenager but you had every right to not want to see him." her silence showed she was unwillingly to say more about the divorce. But she looked him as if she saw with admiration. "And the trust fund? How much is it" he asked with deep concern that was fuel by the admiration in her eyes.

She saw it and relief spread through. He was not at all bad. Rather he was still the same man she had admired. He just was also a womanizer as well.

"Fifteen million as of now. When I open it could gain a bit more but opening it now would cause penalties and I would need my father's approval since he is the guardian of the trust that my grandfather left me."

"You won't ask him to open it for you?" Surely, he thought, would that not be the easiest remedy to her problem.

"I never want to speak to him again." The finality in the tone of her voice made it clear that she not only meant what she said but that the conversation concerning her father was to be over as well.

He wanted to warn her not to make that mistake. That having lost his father there is nothing like word left unsaid that haunt you in the night but he held back. That would reveal too much of himself. The soon to be lovers went back to their light teasing and Chuck was more than happy to make Blair blush.

"So what's for desert?" Blair asked still wishing for more time before they entered the bedroom. She knew she was aroused at this point between the wine and his stares she felt ready but the beating in her heart was making her frightful.

"You," he said and suddenly the room felt like an inferno for the young women. But with no hesitation she stood and walked to where into the hallway she noticed earlier assuming his bedroom was here.

"Last door on the right," he said informing her. She continued on and he followed her. For all the women Chuck had in his life he suddenly felt incredibly excited more so than usually. He was a bit embarrassed to find his palms were sweating wiping them on his pants leg he slowly walked after her. Likening his walk to tiger stalking their prey.

She turned and looked him. With courage and she liked to think with grace she let the thin straps slip off her shoulders as he drunk her in. His stare filled her with confidence as she let the dress fall to her feet. The rich purple and black lace bustier was something of a crop top that left a palm size amount of skin showing before the lace purple and black underwear. He stood no more than two feet from her as he stared hungrily wanting her. Turning on her own accord slowly so he could take her in.

"You like, Chuck?" she asked and he nodded unable to find the words to describe her beauty.

Suddenly it was Chuck who became the prey as Blair approached sliding his suit jacket off of him running her hands over his shirt letting her nails softly graze his chest. She looked up at him a surprisingly innocent stare but thoroughly looking like a vixen in all other ways. Before she kissed him he finally was able to speak. His only word, magnificent.

She giggled lightly before kissing him. She went to unbutton his shirt but that was quickly forgotten as the kiss intensified. She instead grabbed the loose tie by booth ends and pulled with her a she walked backwards to the bed. As he laid over her he took charge running his hands over her body wanting to touch every inch of her visible flesh. Somehow she unbuttoned the shirt fully and pushed it off him. His mouth made its way to her breast and he was more than happy to discover she was very sensitive to his touch. Vowing to make her orgasm before he took things further he moved his hand rubbing his thumb over her center. Without warning he slipped his finger inside of her surprised to discover her tightness even though she was already aroused. His mind drunk with lust took him a few seconds before realizing she was a virgin or at least had very little sexual experience.

Like he was burned he pulled his hand away and stepped back stumbling over his own shirt. In the confusion he fell back onto his bottom.

"Chuck?" Blair asked sitting up in a thick and heavily voice. She was confused as to why he stopped but she wanted more of what he was doing to her.

"Are… are you a virgin?" he asked in disbelief. There was no why she could be in his mind not with the gusto and courage she had tonight undressing for him, kissing him, pulling him to bed.

"Is that a problem?" she asked with a cute pout. Really she held no qualms at this point about having sex with him. Her body burned for him. Frankly, she was a girl whose belief in love and trust in others had died long ago.

"Yes! What the hell! Why didn't you tell me?" he asked as he ran his hands over his face. "Fuck I am such a dick."

"Chuck I didn't think it would matter. I thought you wanted me. Plus, don't guys like virgins," she said her voice cracking as her embarrassment took over.

Chuck unable to distance her from the way he would want his own sister to be treated saw the situation vastly different. But when he looked at her there blushing red on his bed half dress his sister was far from his mind. Unable to think while staring at her he rushed out of the room and walked into his closet. In there he paced the length of the room before standing in front of the mirror in the room. Staring at himself he saw the darkness in his eyes. The lust written on his face. Taking a deep breath he tried to find the energy to think of what to do in this situation. She was so beautiful sitting on his bed waiting and wanting him, he thought so what is wrong. Then he thought back to dinner and the way she seemed distant until she finally opened up. The way she looked at him with lust but the adoration was gone. Almost gone. She smiled her smile at him he remembered when he told her he was putting his lawyers on her mother's case. He wanted that smile now in his bedroom. But it wasn't. In there she was a women like all women who only wanted him for sex or money. He stared at himself as the seconds ticked by. He knew what he needed to do.

* * *

Commentary: The Candidate in the Mirror is the title of the chapter for multiple reasons. It begins with the television acting as a screen between Chuck and the Van der Bilt family. All of these men are living spoiled lives very unconcern with what is happening around them. The women in this chapter are the important to display the actual feelings and emotions around them. Maureen is upset with valid emotions, we hear about the women with the sexual harassment claim that was used by the Van der Bilt family, the unnamed model who steals from Chuck, Anne who is in control, and finally Blair the women hurt by her father is somehow still innocent in this UES world filled with lies and scandal. This is very much a man's world at this point and we will see that tension with the male/female dynamics especially through Serena and Blair as they enter more fully this world.

The model that Chuck brought to Aspen is nameless and very nondescript because she is supposed to be the model (symbol) for all the women that Charles had in his bed. Chuck lashes out on the model in that first scene because he upset that his worth is regulated to sex or money because Blair is on his mind. C is very much more of that Charles persona in that first scene and then Blair forces him to becoming more like Chuck the man who cares about his family and his sister. That throws him off because he is used to distancing his sexual encounters with that Charles persona. The Candidate refers to more than just Tripp it also applies to Chuck who is having to choose in that last scene between being Chuck Bass or Charles Bass. (the Batman v. Bruce Wayne theme)


	4. Baby, It's Cold Outside

Once again thank you to everyone who has reviewed and shown interest in this story. I hope everyone says interested in the story and continues to review.

To the Tripp question. You are totally right. I don't know why I did not I did not realize that mistake before. I have to go back edit that mistake but I guess the name has become more popular after Palin's grandson name.

* * *

He came back out of the closet dressed in a silk pajama bottom holding the matching top. But he discovered Blair was quickly trying to dress and leave. Her dress was half on when he stepped in front of her. The tears in her eyes kicked at his conscience.

Rubbing her shoulders once the dress was down he stopped her from pulling from his touch.

"I am sorry Blair but I want better than this for you," he said in a quiet voice. He knew he wanted her for sure but suddenly the way he had her became just as important. He wanted her respect and at this moment all he saw was shame and anger in her eyes.

"I just assumed that since you are so beautiful and I knew Serena had her fair share of guys that you would too. I know how important for Serena, Dan was for her when she lost her… you know," he mumbled blushing unable to talk so freely about his sister as such and trying to soothe Blair's anger. But his words came out jumbled never experiencing a situation in his life like this.

"I don't want that. I don't want to let some loser into my life just to break my heart. Remember how hurt she was when he cheated on her with Vanessa? I want sex. Unattached sex," she said with unguarded passion surprising Chuck. That nothing blue dress she was wearing was too much to look at so he kept his eyes squarely on her face.

Originally she was angry at his suggestion for sex for money but only because it made her feel cheap. But standing here in his bedroom after receiving his touches, kisses, and caresses she was sure she wanted this. It was not that she wanted to be in love. She really had never meant any man she trusted to even get close to her whether just for sex or for a relationship. Chuck had awoken a new side of her and she wanted to learn more. Suddenly all the men in her life that she never made time for made her feel like she wasted so much time. She wanted of this passion and feeling.

He raised an eyebrow in suspicion. "You are eighteen and easily one of the most beautiful people I have ever met. If you wanted unattached hookups you would have had them already," he said the words out of his mouth before he could think twice.

'Easily one of the most beautiful people I have met?' he wondered to himself. Where did that come from it was only a few days ago that he never thought that. But standing there looking at her eyes watching emotions flow through them he was drawn in. For someone who never showed emotion never felt half of what he saw in her in those moments he was hooked. He never remembered feelings shameful for he had no shame, never felt anger for he was indifferent, never felt passion for one person for he only felt lust for all women he encountered.

She blushed red. How could she say she wanted unattached sex with him without sounding needy. Surely, she thought, she could convince him.

"I don't want to back down on the deal," she said instead stepping back from him telling herself to act once more like this was a business deal.

He smiled a real smile wanting to rid her of her embarrassment. "Of course not."

Her pride he understood. He was just as prideful especially when it came to taking money from others. Handing her the pajama shirt he told her to put in on. Cutely, her eyebrows came to together as she questioned his order. To her and his own shock he leaned closer and kissed her brow.

"You are going to stay and we'll have a sleepover of sorts. You did indeed only promise me a whole night including dinner, desert and breakfast and I will collect my debt of course," he said with a playful smirk.

"Chuck…. Are you sure?" she asked as she twisted on her heels. Honestly, she still wanted him to take her in his bed but she could hardly continue to push the point without in her mind appearing desperate.

"Its late, its cold outside. Really you should stay," his voice was honest and even sweet to Blair ears.

She nodded before answering. "Thank goodness for loopholes," she joked making him smirk.

"I am going to order some desert and you will pick the movie. We can order anything from On Demand or watch Netflix or something," he shrugged.

He was out of his depth. He never sat down and watched a movie with a girl. He never not had sex with a girl he let sleepover. Another rule he had was thrown away yet again. Grabbing his remote he hit a button that allowed a large projection screen to come down and handed the remote to her. When he reentered the bedroom after order room service was order he was happy to find her navigating Netflix wearing his silk pajama top. He quickly wondered if she was still wearing that purple and lace underwear set. Not seeing any on the floor next to her dress or the bed he assumed she was. He took a deep breath. Could he actually just have a sleepover with a girl? Could he actually have a sleepover with one of the most beautiful women he ever met he rephrased in his mind.

"Wanna binge Mad Men" she asked. Nodding his head at her suggestion she smiled and queued it up. A feeling of need washed over the young man. He wanted more. More of her smiles and those teasing looks. The idea of trading more money for another night like this popped into his head. No, he told himself he was no one's sugar daddy or sponsor. He did not need to pay a woman for intimacy. He had no purpose for intimacy he reminded himself.

"So… what did you order?" she asked uncomfortable with the silence but physically comfortable as she lounged on the oversized amazingly comfy bed.

"Brownies with ice-cream and fudge. Keeping it simple," he said with a nudge of his shoulder but he stood at the doorway watching her intensely.

"You still want me," she said breathily with a smirk on her face.

"Of course. But my position is firm."

"Is that the only firm thing in the room?" she teased making him laugh but he remained silent. "I am not your sister. You don't need to protect me."

"You are definitely not my sister. I am not confused about that, kid," he said with a wink. She smiled back with the knowledge of her appeal.

"Wanna have an I.O.U once I meet your 'requirements'?" she said hoping he would say yes. She knew she would never stop wanting him.

The ding of the bell alerted him to the room service that awaited him. Happy for the distraction as a wave of different moments overcame him at the thought of Blair sleeping with another man. Though he encouraged her to that only a minutes ago he now regretted it as well.

The young service attendant who often brought up his food always delighted in the beauties that Mister Bass entertained. One look from the them usually sent his imagination souring. Unfortunately, it had been quite some time since he recalled seeing Mister Bass's entertaining a lady in his penthouse. So he was pleased to glance up and see a women emerge in only a man's black silk pajama top.

"Do you need any help?" she asked with a sly smile attracting both men's attention.

When he was done collecting the plates from the dinner and placing the desert plates on the table he glanced up at the women again pleased with her beauty. Suddenly Mister Bass was standing in front of him a stern look on his face and his hand outstretch with a tip. Understanding quickly that he was facing a jealous man and this woman was not like any other that entertain Mister Bass attention he quickly left.

The two shared their deserts in bed. Once done Chuck stood and whistled. Blair's surprise quickly turned into mirth when Monkey came running into the room. Barking happily as his master when he pointed the bed which meant he was allowed up.

"You do not sleep with your dog," she teased as she patted the mutts head looking at Chuck sweetly. She felt comforted that Monkey would also share the bed with them.

"I do. But you can't tell anyone," he said sitting back on the bed. Monkey took his spot at the end of the bed Chuck on the left and Blair on the right. Due to the size of the bed there was quite a lot of space between Chuck and Blair. The tension between was gone and it even began to feel like a genuine friendly sleepover. At one-point Monkey came over and put his hand on Blair's lap. She petted him not thinking too much about the scene they were creating.

As they watched Mad Men the beginning both appreciating the depiction of New York City in the 1960s and the power of Don Draper. They quickly watched six episodes together laughing together, discussing different theories, aweing over the costumes. In fact, Chuck took notes and was planning to call his tailor in the morning making Blair tease him relentlessly over the fact.

She fell asleep and Chuck shut the television off. Unsure why but he moved closer to her in the bed. Monkey who was at the foot of the bed looked up at him at the moment with disapproving eyes.

"Don't look at me like that, boy," Chuck pleaded with the dog.

Finally, when he was close enough he pushed the hair form her face. twirling a place of hair in his hand he stared. Confused over the events of the day. He was determined to have her this morning and yet his conscience, one he did not know existed stopped him. However, the thought of her taking his advice and falling in love made his breathing harder. For no reason other ceasing the panging in his heart he slipped his hand under her shoulder and pulled her to him. Waking Blair who was more asleep than awake sighed and snuggled closer to him. The panging of his heart only increase further but now a warm feeling spread through him. The half-asleep Blair slid her hands over his bare chest and then pecked a kiss on his chest before placing her head down. Chuck was fearful she would hear his beating heart.

* * *

Chuck woke up the sun still had not rose but he did and left the bed. He was very determined to keep her arm's length away the next morning. He tried to convince himself that it was only because of his over indulgence in wine and sweets that had his mind muddled with false notions of affection. In fact, he told himself it had probably more to do with him allowing her to break rules that he had always followed when it came to women. Case and point the need for the rules. Even still he admitted a small part of him looked forward to breakfast. The table was set once more for their new meal when Blair emerged from the bedroom in her school uniform reminding him how young she was. How could he be so easily enraptured by women who knew nothing of men but she very easily had him a mess.

"Morning," she said. He could tell there was worry in her gaze and he raised his eyebrows in a questioning matter. Still she hesitated.

"Do you need to run off for class?" he asked with a smile trying to appear as if he was not looking forward to this.

"No. Umm. I just wanted to make sure that deal we had" she began to say but he interrupted.

"The money is in the account you gave me," he informed her.

"No. I trust you about that. I just wanted to make sure that the deal remains between you and me. See I didn't tell Serena. While nothing really did happen, I don't want it to get out that I agreed to sleep with you for money," Blair said very straightforward and he was impressed by her bravado.

"Yes. I never kiss and tell," he promised.

She sat down and grabbed some toast. As confused as she was last night she was even more so this morning. The need she felt for Chuck in the midst of their passion was still there but she refused to throw herself his way again only to be shut down. A least for the moment. Blair always found a way to get what she wanted and this time she figured it would be no different.

They idly discussed theories over Mad Men happy to have a mundane conversation. When breakfast was complete Blair in her path to leaving turned back to Chuck with a saucy smile.

"You liked the lingerie I wore yesterday?" she asked teasingly,

"It was wonderful but the wearer was what made it so," he said. He was so smooth she thought but she was determined to have the last word.

"I purchased it especially for you since I know purple is your favorite," she said and she noticed his eyes widen in response.

"Is that so," he said calmly but she saw past it now that she knew his tell.

She was already at the elevator a few feet away when she tossed her hair back and said "Yea, I got it two months ago for my birthday." Before he knew what he was doing he was up on his feet walking to her. Stopping himself only a yard away he coughed trying to suppress the urge he had to kiss her.

"Bye Chuck," she said as the elevator opened. "I'll let you know about the I owe you," she teased.

The moment the door closed she fell back against the wall breathing hard. The last moments spent with him tested her courage but she was able to see how easily she could make him break his resolved. She wondered if only she would have said her words when they sat across the small table from each other. Her eyes closed as she thought of him pushing the table out of the way to kiss her. Coughing she stood tall as the elevator door open to her. She glided out the doors a women changed from when she went in last night but not in the way she expected.

There was something new about Blair everyone would agree in school. She came in full of light a few minutes late to homeroom and Serena looked at her best friend with a questioning stare. She was certain that Blair was going to be bummed out over the money that her mother owed. But Blair came in beaming with a smile that she had not seen in very long time.

It was when they got ready in gym class fourth period that Serena finally got a chance to talk to her best friend.

"Hey what's up. You figured the money thing? You seem like you are in a great mood," Serena asked her best friend filled with concern.

"Yea that sorted out for at least a month," Blair confided.

She texted her mother after she left Chuck's apartment to let her know the money was in the account. So also informed her that one of Chuck's lawyers Cyrus Rose was going to text her and was going to help her per Chuck's instructions. Blair had previously told her mother that she had arranged with Chuck a deal for him to loan them sixty grand. Her mother was a bit worried but she needed the money and was not in the space to ask so many question. She told Blair that she did not need to do this and she would have figured it out but Blair knew her mother was like her. They both had a hard time asking for anything let along a loan. It did not hurt that Chuck was a billionaire so the Waldorf women were not super concerned with the need to pay him back immediately.

"Oh wow that is great Blair," Serena said half hugging her with excitement. Blair suddenly felt the smile slip from her face as she thought how she got the money.

"I feel like celebrating. Club this week?" Blair asked. It was usually Serena who would ask so it was weird that it was Blair suggesting a club night.

"Really. Why?" Serena asked.

"I don't. I want to have fun. Meet somebody maybe," she teased.

Serena stopping the jog that she was running that. "What have you done with my best friend?" she asked her friend.

"What do you mean?" Blair asked laughing continuing to run. Serena caught.

"You want to hook up with some random stranger at his club?" Serena hissed in shock still.

"I am free, alive, young, and beautiful. Let's have fun," Blair said with a wink.

"You sound like my brother," Serena said her eye twinkling.

Blair rolled her eyes and bit but a twinge of pink came to her cheeks.

"I don't know if I can I some stuff planned on Saturday and that college thing on Sunday Maybe next weekend though," Serena hoping that Blair would not press to hard. She had plans for the weekend. Plans she could not tell her friend about. So she pushed on further running faster so Blair could not ask any more questions.

* * *

Chuck could not keep Blair out of his head. It was Tuesday and he was spending his time googling scholarship and trust funds. He wanted to know if he could somehow help. He knew he needed to stop. It was midday after lunch when Charles had a moment of free time that he found himself walking in the corridor that lead to the lawyer's section of Bass Industries. They were two floors below his floor and he never really came down here. Everyone was looking his direction tense and confused as to why the C.E.O of Bass Industries was on their floor. He ignored them all and continued walking the direction of Cyrus Rose's office that he assistant had assured him would be office 1715.

Knocking once he then opened the door walking right into Cyrus's office.

"Mr. Bass!" Cyrus greeted with a smile as if he was expecting his boss's boss to be walking into his office at this very moment.

"Mr. Rose. I expect that you already had the time to contact Mrs. Waldorf?" Charles asked trying to remain aloof and distance from the conversation.

"Yes. Yes, we talked on the phone. She mentioned that you are friends with her daughter," he said smile. Even though Cyrus also smiled it felt knowing and Charles shifted turned in the office to look at the shelves that lined the room. There was a picture of a bird that Charles grabbed quickly.

"Are you a bird lover?" Cyrus asked excited as he rounded the desk.

"No," Charles said putting the picture down turning back around.

"That one if the Blackpoll Warbler. You can see that one in Central Park. As much as I love the rare ones I do enjoy the local bird's species as well. They give me a nostalgic feeling," Cyrus rambled on.

Charles knew it was not a nervous habit. Cyrus was just a happy person. It was why he liked him. He was not afraid of him. His overall good cheer also meant that he would not mind working on a personal favor for Chuck. Of course, BI was paying him for the work but another lawyer might not try as hard. Charles put his hands in his pockets not wanting to hear another bird lecture but politely looked back at the photo and attempted a smile.

"So how does the Waldorf case look?" he asked instead.

"Oh it is hard to say. There is a lot of moving parts but I am sure we can get it handle in a week or so. By then we can negotiate with the lenders and the banks. Fingers crossed we should be able to help them out," Cyrus explained.

Charles nodded. "Thank you for doing this. I hope I am not taking you off anything more important." Even if Cyrus would give his all on a case like this he still may not be interested to.

"Nonsense what is a million-dollar investment deal compared to helping out a friend," Cyrus said with an eager smile on his face. If anyone else would have same that he would have thought, they were being sassy but Cyrus meant it purely out of genuine empathy.

"I suppose," Charles shrugged remaining nonchalant.

"Is this Mrs. Waldorf daughter a special friend?" Cyrus asked. Immediately Charles tensed up.

"I hardly think that is an appropriate question," he told the older man using his C.E.O voice.

"Oh yes of course you are right," Cyrus said.

"She is my sister's best friend," Chuck said suddenly feeling the need to explain himself to the older men and not wanting him to think Blair and him were anything more than acquaintances.

"Well this is very nice of you to do, sir," Cyrus said finally dropping the bright grin on his face.

"So whatever it takes and whatever you need. Full resources on this one. But no one outside you and me know this is happening. Your boss only knows you are working on a personal issue for me," Charles said very businesslike. This was all sent over in the email he had written to Cyrus but he wanted it be in clear in person.

"Yes, yes of course. Wouldn't want anyone to know the C.E.O does favors for friends or their sister's friend," Cyrus said and then he winked. The wink threw Charles off making him crease his brow as he wondered what the older man meant by that.

"Okay. Let me know if you need me to do anything to help," he reminded the man. He was feeling uncomfortable in that room admitting that he was trying to do something to help Blair.

Glancing back at the photo of the bird he picked up he paused for a second before closing the door. He known Blair for nearly half his life. Helping her, seeing her would create a sense of nostalgia and familiarity nothing to worry about he reminded himself if it made him feel a bit warm inside thinking of her.

Later that day in the afternoon a Blackpoll Warbler was watching perched from a branch in Central Park. The days were short and the sun was already setting making it colder in the new shadows. Underneath the stone arch Eaglevale Bridge in Central Park it was completely cast in shadows forcing Lily Van der Bass to rub her shoulder from the cold wishing that she would have worn a more functional jacket rather than opting for a stylish one. She stood under the bridge hoping it would stop some of the side wind.

"You invited me here and you left me waiting. It is freezing," Lily sneered at the man who was walking up to them.

"It can't be as cold as your heart, Lily," he responded rolling his eyes.

"What do you want?" she asked confused as to why they were meeting like this ignoring his jab.

* * *

 **Commentary** : The title of this chapter is from the Christmas (winter?) song "Baby, Its Cold Outside."

So the loophole in the arrangement. A sleepover. I am surprised no one guessed it in the reviews. In Chapter 2 the deal they shook on ultimately was "For a night, the whole night. That means dinner, dessert, and breakfast the next day I'll make it sixty." Of course with the implication being sex none of that yet. Blair at this point just wanted to sleep with Chuck while Chuck is trying to be mature and honestly a little boring. The creepy waiter/busboy was an important because it is the first moment that we see Chuck's jealousy.

Chuck trying to help Blair is making him merge a little of the kindness that is in him into his work life. In this chapter there is a very small shift in his feelings for Blair. Him holding her as she sleeps is supposed to be sweet and a little bit creepy for both Blair and Chuck. Chuck doesn't understand it and Blair never even realizes she snuggled with Chuck that night. Even still Chuck sleeps only a few hours and wakes up before her still showing that he is not comfortable sleeping besides any woman the whole night. Yes, even Blair.

We met Lily and Cyrus in this chapter. This fic is going to have many of the characters from the show in this. Even ones you may never expect. And Cyrus being that happy in front of Chuck is such an awkward scene that I love. Also I do not know if that bird would have migrated but let's pretend it didn't. I also am having fun cutting the scenes in a way they would connect like if it was a show the camera would focus in on the bird in the picture and zoom out to the bird in the park. I am really concerned with not having choppy cuts on scenes and I don't want to use line breaks unless it feels needed.


	5. Love Squared

Thank you for all the amazing reviews. They really push me forward and I look forward to reading them. I tried to respond to all the reviewer who have accounts if any questions were posed. The following response are for reviewers that without accounts or for a comment that would be helpful/fun for the readers.

Alisha, I am unsure what you meant by soft? I think you were referring to Chuck's character and yea he is a bit kinder, gentler in the last chapter. He had some moments early in this fic when his mask is off and we see that a lot in the last chapter and the next two. But I wanted to show that other darker side of him early on as well and we will see more that in the future. I hope this makes sense and clears up any confusion you felt with the Chuck character.

To the reviewer who mentioned Blair confidence in the last chapter you are totally spot on. I really did not want this Blair to struggle with her appearance/looks rather her struggles are going to be more external in this fic with money, her father, Chuck, Serena, and other characters. Sorry, there is not much C/B progress in this chapter.

Pettycharlie, your "Chuck is clever, caring and so man…" review made me smile and laugh. And then I reread his scenes from the last two chapters and I was like woah he is But I like it. I hope it is not read as Out of Character.

iAlliegator, your comment about Chuck willing to be let go himself to feel "like/love apart from his money and sexual prowess" deserves mention because that is such a major character development I have for Chuck. Really, this is going to a major storyline even outside of Blair as he internally discovers that he doesn't really know how interact with women without money or sex.

* * *

Love Squared

Nate, Serena secret boyfriend, was curious as to why his best friend was in a slump. Nate knew Chuck for years and the only time he remembered Chuck more downcast than this was when his father died. They were having lunch Wednesday after Chuck delivered a guest lecture speech for undergrads at the university.

"That women at the bar is eyeing you," Nate smiled at his friend over the table as he admired the women's beauty.

"Not interested," Chuck responded not even turning to look. His expression looked like he tasted something bitter and that was how it had been since at the end of the speech.

"Something wrong?" Nate asked as he pursued the menu. Chuck always got into the best of best restaurants so choosing was a very hard choice for the young man. But, Nate could tell something was bothering his friend so he kept one eye on Chuck to see if he gave anything away.

"Nope." The tight smile that Chuck gave was forced and Nate wanted to laugh but knew better.

"Did that chick from Aspen give you herpes or something?" Nate whispered entirely serious making Chuck frown further.

"If she did I would have sent her straight to you," Chuck bit back with more anger than he meant.

"Foul, man. What the fuck, man. You are acting like someone shove a stick up your ass," Nate responded his anger besting him as he placed his menu on the table to fully focus on the pissed man in front of him.

Chuck rolled his eyes and crossed his arms trying to deflect the attention away. "You know I haven't seen you pick up a chick in a while." The astute businessman said.

Suddenly Nate began to sweat. Is that what this was about, he wondered. Did Chuck somehow find out about him and Serena. He knew it was wrong and against guy code but fuck she came on to him. Now, after months of dating, Nate could not give her up, she was the best thing in his life.

"I am busy with school," Nate responded weakly.

Chuck smiled. "You probably lose your man card and have some silly girlfriend," Chuck said teasing hope not to avoid an argument. Nate was still on edge but slightly less so. Chuck was blunt and he would have said something by now. Unless he is trying to catch me lying.

"Maybe." Nate tested Chuck's knowledge.

"Seriously?" Chuck asked a bit surprised at his friend.

"You'll meet her when the time is right," Nate said with a shrug trying to play off the idea of a girlfriend with the hope that Chuck would never mention it again. "But what about you?"

Chuck groaned and decided to share a bit of his frustration. "I maybe almost had sex with Blair." He had no intention of mentioning the Waldorf money problem or Blair's deal with him.

"Dude you just have blue balls. Try again and make sure whatever interrupted you is gone this time," Nate said happy he could help his older friend.

Rolling his eyes Chuck responded leaning over the table in a whisper. "It's not that. I stopped it 'cause she was a virgin."

Nate really wanted to laugh over Chuck's whispering but instead restraining himself to a chuckle and he could see it angered the billionaire. "I am surprised that she is but you could have made it great for her. Probably ruined it for us mere mortals," Nate said with a laugh that finally came out.

"You wouldn't understand. You don't have a sister," Chuck finished off shaking his head before sipping from his water glass.

"Dude, she is not your sister. Don't pretend you think of her as one. Cause if you did you would have not been anywhere near close enough to her to know she still is a virgin. Seriously man, the way you were looking at her and the way she was looking at you at St. Lucia it was only a matter of time," Nate said before looking around and whispering closer to Chuck. "Plus, I know some of what happened that night we went to the club and…"

Suddenly Chuck eyes flared. No one was supposed to know about that. Ever. Nate instantly noticed the darkness of his friend's eyes and the grip that threaten to bend the silverware on the fork he was holding.

"We don't talk about that. I don't care what you think you know" Chuck said betraying his emotions. Nate had to no way of explaining without bringing up his relationship with Serena.

"I saw some of it," the young man lied.

"Why mention it now?" Chuck asked his anger almost at a tipping point.

"I saw how much you cared about her then. You won't do anything to hurt her. I know you won't. She probably knows you won't either which is probably why she willingly to have sex before you stopped whatever was happening," Nate said genuinely hoping to diffuse Chuck's anger.

Chuck was too embarrassed to mention that Blair had no feelings for him and it was not about trust. It was greed and lust. With a nod Chuck changed the direction of the conversation trying to put St. Lucia out of his mind.

* * *

On a Saturday morning midway through the month of January a serious Blair was sitting in her room researching scholarships. Chuck had texted her soon after their almost night with his private number the information concerning his lawyer that he wanted her to pass on for her mother. It was the first time that she had the privilege of the Bass CEO's private cellphone number. She knew from Serena he had closely guarded it. So it was a bit surprising to receive the text rather than an email which she thought would have been a bit more businesslike. He even encouraged her in their text exchange to call him if she or Eleanor had questions.

Handing the information and the sixty thousand off to her mother was easy enough. Blair presented as a loan to her one she was going to repay when her trust was open. Eleanor was embarrassed to take it but Blair had overplayed the notion that over the years Chuck and her had become good friends. Her mother took the bait and quickly changed lawyers as well. There wasn't a day that Eleanor had not come home smiling talking about the amazing Cyrus Rose. Blair was surprised to find her mother in such good spirits or even interested in another lawyer after her father. She was even a bit angry that her mother seemed to be romantically interested in a man after her father. How she even trust men any more, she wondered not only was her husband secretly gay but he had numerous affairs in the very same industry she worked and employed others?

Pushing all those thoughts out of her mind Blair instead was researching Philip Cooke, who sat on the board that at Columbia that gave scholarship to incoming college freshman. It was the only award for undecided freshman that covered full tuition and Blair was determined to win it. Sitting at her computer she discovered that apparently Professor Cooke was the dean of the business school and mentor of sorts to Chuck Bass. Blair knew that a letter of recommendation and an introduction from Charles Bass, CEO of Bass Inc. would help her enormously but she was afraid to ask. She did not want another thing to add to the things she owed him but then again it was not like this was money. She sat at her desk twirling in the desk chair running over the pros and cons. When the thought of speaking to Chuck again became a pro and made butterflies run through her stomach she got up with a sigh and began pacing the room. She thought of sending an email but was afraid it would get lost in all the other since she only had his business email. Finally, after a deep breath she dialed the number. Part of her hoped he did not answer.

He did answer after only two rings.

"Blair?" he asked sounding surprising rather than saying hello. Stupid, Blair she thought he probably never actually meant that you should call. But he was happy to hear from her.

"Is this a bad time?" she asked wondering if there were some women in his bed from last night still.

"Not at all. How have you been?" he asked surprising her with his cheerful tone and his question even indicted to her that he had plenty of free time.

"I am okay. And how about you?" she asked wanting to appear polite. She was asking him to write her a letter of recommendation after all she needed to be on her best behavior.

Finally, after a few pleasantries later she had the right moment to ask. "I was researching scholarship for college next year. There is a freshman scholarship that offers full tuition and I saw online a few pics of you and Dean Cooke who chairs the board for the scholarship. So I wondering if you would be willingly to write me a letter of recommendation?" she asked crossing her fingers as she paced the room. Her entire next year could depend on his answer.

He chuckled sensing the panic in her voice. How could she even think he was deny her anything? "On one condition," he said.

"Anything," was her response and she meant it. She briefly wondered if he would ask again for sex. She perked up hoping that he had changed his mind

"Have lunch with me sometime this week," he said forcefully as if it was not a request at all.

"Mmm. I have class. I only get an hour lunch break off campus if that works for you," she reminded him.

Chuck felt silly for forgetting that she indeed was still in high school. It was like the reminder threw him back a bit. She was still so young. He should back down. Pursue her later. Not now.

"I forgot," he admitted but was silent making Blair slightly nervous for some reason she did not understand.

He sat at home bored on Sunday morning. He had pulled a 70-hour week at work. His assistant and secretary practically forbid him from coming back to work. It was just that ever since his encounter with Blair picking up women felt cheap. He was reminded how he almost bought his sister's best friend virginity and that always came back to him like a punch in the gut. He took a deep breath. He knew he needed to make things right with Blair or it seemed like his libido was going to be gone forever.

She on the other side of the phone call was twirling in her desk trying to figure out if she should suggest a lunch location that would be suitable for a billionaire and that was close to her school but not filled with Constance students.

"Umm…" she said just to fill the silence.

"Lunch on Wednesday works for me," he said over her. He always kept Wednesday lunches open for family or for work emergencies. "We can invite Serena. You guys can pick the place" he then added. He told himself that Blair was just a family friend it made sense to invite his sister.

Blair's smile fell a bit. Lunch with Serena. It suddenly seemed so different from their shared intimacy last Sunday night.

"Yea that works."

"Okay I will text you my email so just send the information there and I will have that letter of recommendation ready for you. Make sure you toss in a few of the things you would like me to mention"

"Thank you again. I will see you Wednesday."

"Blair," he said stopping her from hanging up. But then he was silent.

"Yes?" she asked confused and suddenly excited and nervous.

"I could give you the money for your tuition. It is not a problem," he said. It was almost a whisper as if he could not understand himself why he was offering her so much.

She knew six watches in his collection totaled the equal sum of her college tuition for four years. It was not a big deal to him but it was to her. Waldorf were an old family, her father's family who emigrated to New York from England in the 19th century. The line included Astor, Rockefellers, as well Dukes and Barons dating back to the 12th century in England. She was filled with pride deep pride. The family crest was sewn onto her blanket as a child. She felt like she was undermining that line by accepting such a large handout from Bass. Doing so made her feel like it allowed her father to say I told you that you are not a Waldorf without me. She wanted to prove to herself that the name she was so proud in meant more than her father. Taking the tuition money without earning it would be only second to taking it from her father.

"No," she said her voice stern and clear.

Chuck nodded understanding her pride but found that as much as he admired it, it could be her downfall. So instead he mused over the idea of helping her in a different way. It took him all of two seconds to decide to create his own scholarship for his alma mater. Yes, a four-year full tuition ride to Columbia for undecided majors he thought from The Bass Education Fund. They usually only gave out scholarships for legal, business, economic, and management majors but Chuck thought an explanation would be helpful and looked upon graciously in this tough economic times. It was an easy P.R sell and he wanted to help Blair anyway he could be thinking that the guilt he felt for propositioning her would vanish with his good deed.

Across town, in a hotel in the Meatpacking District a very different couple laying lounging limbs intertwined exhausted from early morning sex. Serena and Nate had been seeing each other since that summer. While they knew of each other for years it was that summer in St. Lucia when things changed for them. After the horrible night, Serena was left alone her best friend and her older brother were too preoccupied to be of comfort, and her younger brother was fast asleep. She found herself in her Nate's room. He comforted her that night taking things no further but the tension was undeniable and Nate suddenly felt protected and concern for Serena in a way he never imagined he would feel. When they arrived back home in New York they began to text each other which lead to flirting and then finally secretly they began to date. Nate was adamant that Chuck not find out at least until they were sure they were 'serious' about this. Six months strong Serena wanted to tell Chuck. She was tired of mid-class hotels and lying to her family. In a show of support, she even decided to not tell Blair about her and Nate but she was worried her friend was suspicious after blew off Blair for yet another weekend.

"I want to tell people," Serena said bringing up the subject yet again.

"I am worried about Chuck's response."

"Is this serious to you or not?" Serena asked with anger. She was annoyed that they had to spend the holiday season secretly exchanging gifts. She wanted people to know that Nate was hers. She wanted Facebook relationship status, she wanted him to kiss her in public and hold her hand at her in her favorite restaurants.

"It is. I want to tell him. But at lunch last week he was using your friendship with Blair as a reason why he had to end their hookup midway," Nate explained.

"Blair and Chuck did not hookup, she would have told me," Serena said raising up a bit from the bed she was lounging on in disbelief.

"You didn't tell her about us," Nate dryly commented. Raising an eyebrow at her lover she got up from the bed walked to the bathroom to freshen up.

"Serena you can't mention it to her or Chuck. If you do they could figure this out," Nate reminded her when she came out of the bathroom.

Rolling her eyes, she told him that she would not mind that outcome. He felt her frustration. Her understood it but he was not sure that Chuck would understand this. For Nate as much as he hated to be political calculating regarding his feelings for Serena or his friendship with Chuck he needed to be. His father and grandfather were constantly reminding how great it was that he was friends with such a wealthy man and how much that could help in the future when it came to fundraising. Losing this relationship or straining it could hurt his political ambitions. He was breed to be a president or a senator at the least. Not only would Chuck be angry about his relationship but his family certainly would be as well. Serena was thinking about majoring in acting and she was a notorious party girl. She had been detained twice for under drinking both scandals Lily hid but he knew that the media could easily find. The reason all of this was concerning for Nate was because he was more than in like with Serena. He knew it was love but she was two years almost three years younger than him and a free spirit. She could have no clue that he was already thinking of their lives together. However, her bohemian party girl lifestyle was an odd match for his cookie cutter political preppy clean cut image. So when he meant if they were serious he really meant it.

"I am not going to mention it. I promise," she told him kissing his forehead. "You don't need to go on the admitted tour thing with me, babe. It is in public," she mocked but Nate only nodded earnestly making Serena roll her eyes at his misunderstanding of her sarcasm.

Yet, Serena wanted to be taken seriously. She was tired of dating random guys and getting her heart broken constantly. Her first boyfriend Dan cheated on her and broke her heart when she was only fifteen and ever since then she had not had a serious guy in her life until Nate. She quickly finished getting dressed. She was going to be late for her tour of NYU that Nate was supposed to join her on but she suddenly wanted him nowhere near it.

"Nate, you have until March to decide about us or this ends for good" she told him before leaving. It was an ultimatum. She afraid he would back out of this and the worst part of that would be suffering alone in the heartbreak since no one knew about them.

With fear and some hope Serena found her way back into her penthouse crossing her fingers the whole way there as she was optimistic that Nate liked her enough to tell her brother the truth. She understood the fear that Nate had in telling Chuck hell she was a bit afraid herself knowing how protective he could sometimes be. Chuck Bass and the Van der Woodsens were not always close but in recent years their bond was fierce.

So when Serena came home that day from seeing Nate she should have not been surprised to find her big brother sitting in her living room. She wondered briefly if he knew about Nate and her gut twisted at the guilt she felt for lying to him.

"Serena," he greeted easily smiling and standing when she entered the room.

"Hey Chuck, what's up?" she asked still standing far from him. She cursed herself for not showering at the hotel but the water pressure sucked there. She was anxious that Chuck would smell Nate on her. Sometimes he was a ninja when it came to figuring people out.

"Serena you are home," Lily greeted as she came from the hallway. "How was the weekend with Blair?" she asked and she saw Chuck's eyebrow raise up in suspicion. Was Nate right about Chuck and Blair, she wondered as she answered her mother lying smoothly.

"She is great. I was going to get ready and we were going to meet up to the NYU admitted tour thing. But what are you up to today?" Serena asked hoping she appeared calm.

"Nothing. I just need Charles's help with something," Lily said. Serena felt the attention her brother was giving her shift to concern for Lily.

"Lily, is everything alright?" he asked feeling the need to protect his family as the oldest male.

"Yes, yes. I just need some information," she said and smiled at her children. But her non direct answer made it clear that she did not want Serena in the room.

Serena sensing the need for them to talk in private and her need to wash up said her goodbyes and made her exit.

"Lily, whatever I can do," Chuck began to say as he placed his hands inside his pockets squeezing his fist closed as the tension began to fill up.

"Oh, no Chuck, do not worry. I just need your private eye's number," she said feeling a bit foolish. She could have done this over the phone but she knew Chuck would have never rested until he found out what she wanted it for. He was like his father in that way.

"Is anything okay though?" he asked again.

"Yes. It is a personal matter. One I will tell you about when I am ready. So please do not snoop or double pay the private eye for the information," she warned him. "Promise," she said when he did not reply.

"You'll tell me if you need anything?" he asked instead and she nodded. "Fine, I won't snoop or whatever you call it." He promised her.

Tucking a strand of loose hair back behind her ear she then asked "what is bothering you?"

"How did you…" he trailed off realizing how easily he was fooled by Lily's manipulation when she smiled as he confirmed her suspicions.

"No pocket square," she pointed out and he rolled his eyes.

"Come on let's grab lunch and you can tell me about what or who is on your mind," Lily told her son.

"Yea we can talk about what is bothering me after you tell me what is bothering you," he replied. They went to lunch and both avoid whatever was on their minds.

They were gone before Serena left to the tour. "Thanks for coming with me," Serena happily told her best friend hugging Blair from the side as she walked with her in the crowd of other students who were touring NYU. She had called up Blair and asked her to come with.

Serena had gotten into NYU even though it was her lifelong dream to go to school in Los Angeles. In fact, up until it came time to apply to schools Serena was determined to leave New York. So both Lily and Blair were filled with excitement that Serena might be staying in the city for college.

"Hey anything to get you to not fly miles, and miles, and miles away," Blair pouted at her friend.

They were currently on a tour for admitted students and Serena was paying close attention to the tour. What further surprised people was the fact that Serena had applied to Stern Business School at NYU one of the best in the country. She had inherited a fair number of stocks from her late step-father's company and she was promised a place in the company if she wanted. It was just that no one, probably not even Bart, even expected her to want to pursue a business career. In all honesty, Blair thought Serena would have been interested more in the acting school.

To Blair, this all meant that Serena was changing or trying to change for someone. She was suspicious that her friend had a boyfriend and she knew Serena would tell her eventually. All that mattered to her was that Serena stood in New York City.

"This true. We could even live together if I stay," Serena teased Blair. However, she was also wondering if her friend had her own secret relationship.

"Sure, unless you are already planning on living with someone else," Blair said raising an eyebrow at Serena figuring if she staying in the city for someone she would surely live with her partner.

"Unless you are," Serena threw back at her best friend. They had stopped and looked at each other waiting for one of them to back down. The tour was walking away from them but each girl wanted answers.

"Nooo, but are you?" Blair as she raised her eyebrow at her friend extended her words to stress her point.

Serena not use to keeping secrets of this magnitude for this long and filled with fear over her impending heartbreak at Nate's refusal to tell Chuck she decided then to share her secret. Turning back to the departing group she decided she did not need the admitted tour. Plus, she could walk around the school whenever she wanted. Then again, if her and Nate broke up the NYU dream would be pointless. Linking arms with her best friend she took a deep breath and said "There is so much I need to tell you."

"So you are dating someone," Blair smiled happily with her friend. Serena always had men flock to her but she had not had a serious boyfriend since Dan cheated on her about two years ago.

Serena refused to talk about it in the middle of the street and decided they should pop into a coffee shop near Washington Square Park to chat. Blair was so not in the mood to be in the village with its vibrant bohemian vibe and overpowering sounds packed into tight streets. But Serena kept pointing out the coolness of it and how great it would be to go to school in a neighborhood that was so New York. Blair tried to be supportive. Anything to keep Serena in New York she thought.

* * *

Commentary: Love Squared is simply in reference to the four main characters who are finally interacting in the major ways that they will for the rest of the story: Serena/Nate, Serena/Blair, Blair/Chuck, Chuck/Nate Chuck/Serena. I debated with placing the Bass/Van der family history in this chapter but I pushed it to the next chapter. It is important that we see the way in which Chuck interact/why he interacts with his family and that protection he feels the need to supply for them. The family vacation is going to be continually mentioned until I finally do the flashback on that which is not going to be for a while but clearly something went down so don't get too annoyed if I reference it twice or once in every chapter.

Nate's political motivations are stopping him from admitting to being with Serena because he can't imagine her being a politician's wife. Serena is already willing to give up her dreams of acting and go to school for business for him since she is also already concern with the same thing. I tried to imply this in the story but not state it as directly because I think as a teenage girl Serena would not have even realized how much she was giving up herself in doing this. As I mentioned earlier Serena/Blair are definitely going into a man's world type of feel in which they are going to need to fight to find their own way through. Which is why I decided to end the chapter right before Blair and Serena have that conversation regarding Nate and Serena. In a way a secret that like that was pulling them apart as we saw in the last chapter when Serena can't hang out with Blair and Serena is literally running away from Blair in gym class to hide her reasoning. It is only when face with the pending end of her relationship does Serena finally become willing to admit this relationship to her friend.

The Chuck and Blair arc is slow moving in this chapter. Chuck is dealing with his feelings that he is labeling as guilt Blair is interested in Chuck but not overly so. Chuck does have a moment when he questions Blair's age and his pursuit of her. In general, five years is not that big a deal with age gaps all things considered but the teenager in high school thing is the issue for me. The age factor is important and will be raised again by them and by outsiders. I feel the need to address it in the story and highlight that Blair is still in high school and Chuck is running a billion-dollar company so they aren't actually peers or equals. Chuck is in a power position as we have already seen in his attempt to purchase sex from Blair. Also it allows me to work with Blair who is coming into her maturity so she does things a bit more reckless than someone's Chuck age would and Chuck's maturity is needed in order to have him me this confident overbearing (manly?) figure.


	6. Sugar and Spice

Thank you for all the reviews and responses to the story. I so glad that many of you enjoyed the Nate/Serena bit of the chapter. Many times secondary couples are not as engaging so I was overjoyed to see that so many of the reviewers were interested in them.

I received a review that complained about the lack of forewarning regarding to the OC/age differences in the character. However, I did give a clear warning in the first chapter. I suppose they missed it. So I would like to take this time to mention yet again that Blair is a bit O.C much more so than the other characters. She is still determined, fierce, very intelligent, bossy, and often misguided by her own pride. But she is going through a learning curve. The age differences are essential once again to the plot of the story. I cannot see the Chuck I wrote in this story acting in the way he does unless he was older than Blair. With any AU story the character's personalities do shift because the characters are reacting to situations they did not encounter in the show.

I was also accused in the same review of not caring enough to proofread my story. I re-read each chapter at least half a dozen times before posting. I know I do not catch all the mistakes. I have dyslexia which many people do not understand affects writing as well as reading. So misplaced/misspelled words especially homonyms can be found in my writing which I am unable to catch when reading. Since dyslexia also affects my ability to sequence a word two or more spaces over where it should be cannot be caught by my proofreading because reading for me occurs differently than does who are not reading impaired. But I promise I do care greatly about my stories and I am offended that I would have been accused of not caring.

I do not want my defense above to take away from any criticism that is merited. I greatly appreciate any review left, positive or negative.

* * *

 **Sugar and Spice**

Finally, they were able to find a fairly large coffee shop that was not too overcrowded with students. Various fabric hung over the walls and the music record art that was stapled to certain locations. The mismatched chairs were to be part of the style creating a uniquely neo-hippie store in the days before the full hipster vibe took over. Blair's preppy ensemble felt out of place and not in ambiance with the store but Serena and her long blonde hair, brown messenger bag, army green parka coat over a bohemian loose fitting dress made her look like she belonged. Then again, Serena managed to look good in any environment.

"Serena don't forget the sugar in my coffee. It will be needed to over mask the probably horrible coffee here" Blair reminded her friend who gave her a look that read how could I forget. She did not even take the effort to lower her voice uncaring of the glances that were shot her way. She figured these people never had a real cup of imported Ethiopian espresso.

Serena ordered their drinks rubbing her hands enjoying the warmth of the shop smiling at the barrister as Blair looked displeased as she claimed two seats in a corner for them. Janis Joplin Piece of my Heart was softly playing in the shop making Blair perk up and she secretly swayed her foot under the table to the rock and roll blues rendition of the song.

"So tell me what's going on?" Blair asked once more as Serena sat down two coffees for her and Blair.

"I am dating Nate," Serena admitted and released a breath of air. She grimaced as if waiting for Blair to yell at her but also felt relief.

"Chuck's best friend?" Blair asked to be sure.

"Yea." Her response was meek.

"And Chuck doesn't know?"

Serena shook her head. Blair sat back and pondered the new information.

"After that really crazy night on vacation. I went to him that night needing to speak to someone who wasn't there and we just talked. We talked until I sleep and he just held me. We agreed it was we should not start anything because of Chuck but then we kept texting when we got back to New York. Pretty soon we couldn't not you know end up together. By September we were dating. He is afraid to tell Chuck. I was with him this weekend… not visiting upstate like I told you and I gave him an ultimatum. He has till March to tell Chuck or it's over," Serena said volunteering information as her friend was silent.

"So you won't stay in New York if you aren't dating him?" Blair asked. Her concern first with her friend being miles away. Blair was used to putting her needs first. But there were plenty of moment when she protected her love ones and put them first so fully that there was no doubt that loyalty was paramount to her.

"I am not sure," Serena confessed.

"You love him?"

"I think so," she said while nodding.

"Then you should tell Chuck. But if you know when things get out in the open you may feel differently about the situation. The mysterious air will be gone," she said trying to caution her friend knowing that Serena was often ready to leap with her heart not her mind.

"No Nate would hate me. Apparently Chuck has made it very clear I am off limits. But maybe there is hope because Nate mentioned that maybe you and Chuck might have a thing…" Serena trialed off. Her face looked frightened as if Nate was going to appear from around the corner and discovered she spilled the secret not even 24 hours after being told not to.

Blair always one to be really for anything revealed nothing in her composure. "Oh my god, no. You know I had a crush on him since forever but come on its Chuck. He probably got confused because… I didn't want to say anything before but Chuck is the one who gave me the loan," she said moving in closer like she was confiding in Serena to butter up the half-truth. It was only half a lie, she thought. It was believable that Nate would in fact confused such a thing so Serena nodded and quickly believed her friend and in the goodness of her brother.

"That is so sweet of Chuck. But, I was really hoping he was into you. Maybe then he would stop sleeping around with all those skanks," Serena said with a shrug of her shoulder as if Chuck and Blair dating was no big deal. But Blair's stomach was twisting at the thought. She pulled back and took a sip of her coffee. Titling her head as if to think about it she moved in closer once more. "Plus, I always thought that maybe something happened in St. Lucia. You guys did spend the whole night tonight. We never really talked about it besides you know you telling me that you did not want to talk about it," Serena added on moving closer in speaking even softer tones.

"I still don't," Blair reminded her eyes fierce and sharp.

Serena nodded and began to talk about NYU and Nate as the girls moved back and forth between the two conversation with ease. Years of friendship made it easy to talk about two subjects in way that no outsider would have been able to keep up with.

Unknowing to the two women they smile and laughter attracted the attention of the barrister at the coffeehouse. Hearing a few mentions of NYU where he was currently recently accepted into the graduate school he knew that he had a way into the conversation. Really it was the brunette who while talking was tapping her foot along to the beat of whatever song that was playing. When she first walked in he thought she was a rich spoiled girl. But here she was in enjoying his playlist. He was a music production graduate student at Tish and worked part time at the coffee shop. The moment Moon River one of the greatest Movie Songs in his eyes of all time played her eyes light up and he watched as she sang the first two lines making her friend laugh. He was hooked.

Under the guise of picking up their coffee mugs he walked over hoping to start a conversation.

"Hey, I heard you are talking about NYU," he offered to the girls. The brunette rolled her eyes and but the blonde whose order he took smiled up.

"Yes, do you go there?" she asked knowing the neighborhood was filled with students.

"Soon at the graduate school in Tish. For music production," he said while looking at Serena but quickly turning his attention to Blair saying a bit softer, "My playlist is playing in the background."

Serena raised her eyebrows to Blair in a manner that meant he is into you. Blair usually knew that most of the guys that approached them were into Serena not her. She ignored her friend.

"That's great. I am sure you can tell Serena so much about the school since she is planning on attending for the fall," she said pointedly at her friend.

"Actually I can't. I just moved to New York like three weeks ago. When the fall starts up I will be an official graduate student. So I am free for a few more months doing odd jobs on sets and mic work for some small films," he offered. He knew the girls had to be eighteen and he would have thought a bit too young for him but there was something pulling him to this table.

"I am sure you will figure your way around," Blair said.

"Blair and I are lifelong New Yorkers. I am sure she will love to give you a tour," Serena said still in her I am matchmaker attitude. Blair rolled her eyes.

"I actually have a checklist. Of all these great New York movie locations I want to check out. The city is big and the subway is bit confusing." Blair perked up at the mention of a list. She had a similar one for other cities in the world. She loved old movie, especially romantic movies and she was suddenly interested in the conversation.

"Like Tiffany's, the Empire State Building, and the New York Public Library," Blair said finally smiling.

"You heard my play Moon River so yes Tiffany's, and of course the Empire and what movie do you mean with the New York Public Library," he asked happy she was smiling.

"Ghostbusters, obviously," she teased making Serena laugh and explain how obsessed they were with that movie and how her brothers made them watch it endlessly.

"One of the most commercially successful songs from a movie. How could I miss that one?" he joked. Pausing for a moment in hesitation he said, "I am on my break can I join you guys?" he asked not wanting to sat unless invited.

"Depends what movie you meant by the Empire State Building?" she asked.

"Sleepless in Settle," he offered but he knew it was the wrong answer when a smiling Blair shook her head with a laugh. "An Affair to Remember" he corrected making her laugh and nod her head to him joining them.

"So, Scott," Blair said his name dropping from her lips sweetly as she read his name tag "where else are you dying to see in the city." Finally embracing her inner flirt Blair gave him her full attention laughing at his jokes sharing stories about Serena and her, and talking easily about classic movies. She had him hook line and sinker. This new fun and flirty Blair that Chuck helped unleashed was a forced to be reckoned with.

* * *

It was Wednesday and the girls were meeting in the courtyard to walk the four blocks to the sushi bar for lunch with Chuck. While it was cold the bright sun helped warm them a bit. Even still, the girls power walked to restaurant spending little time on conversation waiting to get into the warm environment. Taking a cab in the middle of the lunch rush would take double the time walking would so the girls gritted their teeth and waked on.

Chuck was awaiting them with a glass of sweet wine sparkling champagne raised to his lips as he scrolled through his phone reading over the recent memo his director of communications sent him only moments ago. The champagne was for the girls since he wanted to share with them the news of his new scholarship effort that was opening up with Columbia. The director of communications wanted to have a gala to announce the new fund.

Once they were seated the sever quickly poured the girls their glasses of the sparking champagne not asking for ID. It was an eight hundred bottle of champagne Chuck knew they would have served it to dogs if that was his desire. With the menus handed out Serena smiled and asked her brother what were they celebrating.

"Bass Industries is going to be creating a scholarship fund with Columbia that branches out of our usual business only major in celebration of this being the year that I finally receive my masters," he said raising his glass but no one joined him.

Chuck, was confused, having no knowledge that Serena knew from Blair that Chuck had lent her best friend money and from Nate that Chuck may have feelings for Blair. Serena read right through his brother's announcement. He was doing this clearly for Blair. Blair embarrassed because she knew what was running through Serena's mind said nothing but her mouth did open a bit in shock.

"So we are not into charities, huh?" he asked trying to pretend to be amused at their silence but secretly was annoyed.

Feeling the need to lower her voice Serena leaned in closer to Chuck who was sitting across from her. "Is the scholarship," she turned to look at Blair and then back at her brother "for Blair?" The dimmed lighting in the restaurant hid his faint blush. Blair grabbed the glass and raised for a toast instead finally in control of her emotions.

"To Bass Industries and their generosity. May the best student who applies receive the scholarship," she said and finally their glasses clicked together. She had hope to diffuse the tension at the table.

"There is actually going to be three scholarship of different monetary sizes," he added rather awkwardly. He wanted to know what Serena knew and why tie at his neck made him feel like he could not breathe easily.

"That's wonderful but I am really setting my sights on the Cooke scholarship. I received the letter of rec Monday. Thank you," Blair said and from Serena's surprise Chuck realize that Blair was still keeping some things for Serena. Chuck would rather not have his sister know what an ass he was for trying to buy sex from her best friend.

"No problem," he said sounding very much indifferent to her praise to him to Blair's annoyance.

The letter of recommendation was beautifully crafted and worded that complimented her and her accomplishments. She found herself after reading it wondering if Chuck himself wrote it or if he passed it on to one of his staff. Were the flattering words his or those of a stranger? Feeling the need to step away from the table she waited until the orders were taken and the conversation changed to Serena's NYU ambitions. She excused herself from the conversation to go to the bathroom.

Breathing deeply, she stared at herself in the mirror. What the hell was his goal in this scholarship? She told him he did not want a hand out she he created a way to give her handout and himself a tax break. And Serena's face she totally knows something is up. Realizing she could not leave them out there along for too long she reapplied her lipstick. It was a reddish brown with a hint of a shimmer called Sugar and Spice.

"He is just being nice," she said as she stared herself down before puckering her lips at herself.

She repeated the words once again to herself this time as a question. He is being nice? Why was he being nice? She wondered. He was not a man who did something for nothing. Again her stomach twisted. This time she was nervous not because of his aura and good looks but instead because if he was being nice to her without expecting anything in return she had to wonder if he saw her similar to Serena. She knew that he would do anything and pay any price for his siblings and she desperately did not want him to think of her that way.

Meanwhile, the moment Blair stepped away from the table Serena quickly asked him about Blair.

"Why are you being so nice to Blair? She told me about the loan you gave her for her mom and the house," Serena said carefully to her brother watching for any tells he might give off.

"She is your best friend. I have known her for as long as I knew you. I am just being nice," he said his bored gaze drifting from Serena to beautiful women who refilled their glasses of champagne.

Rolling her eyes, she said "you never cared about my friends before."

"She is the only friend you have with a brain," Chuck teased and a smirk appeared on his face. Serena shifted her head reading him.

"A brain? I thought you were a legs man?" she said half teasing her brother half still curious.

He chuckled at his sister. "It's nothing like that. Plus, she is your friend. That would be too weird even for me," he lied easily. At that point Serena became too uncomfortable with the conversation since it reminded her too much of her troubles with Nate and quickly changed it to how their mother was doing.

"Mom is going super senile about a family dinner this Friday," Serena said.

"She said nothing to me," he shrugged. Chuck tried to stop over for dinner twice a month at least but with the recent holidays he had yet to go all of January. "But maybe I will stop by, maybe she is bringing a new boyfriend or whatever." He shrugged.

"I hope not. I hate those dinners," Serena said scrunching her nose up in distaste.

"Those are the worst," he agreed but in his mind he resolved to go wondering if this dinner and its importance had anything to do with her recent need for a P.I.

When Bart and Lily married Chuck was twelve, Serena was seven and Eric was only five. Chuck, refused to allow any of the Van der Woodsens to call him Chuck to them he was Charles. He stood in his room or out always hoping to avoid the so called family that his father wanted. It was Eric who broke the ice at first a few months after the marriage. They need a last minute babysitter since Serena was having her flute recital. So Chuck stood watching Eric somewhere in the middle of night Eric was granted the right to call his new big brother Chuckie and from there on became his shadow. Chuck pretended to hate it in front of his friend but he loved the admiration. Eric wanted to dress, talk, act, and basically be Chuck. It was around this time when Bart pulled Chuck into his office and explained to him that he and Lily were going to legally adopt each other's children. He also explained to Chuck that he was a big brother and it was his responsibility to protect his younger siblings. A role Chuck took very seriously. He protected them like they were blood and to him they were.

At fourteen, Chuck was sent to a private elite school for young men, where eventually he met Nate, and became further involved with alcohol, drugs, and women. At sixteen, Bart died in a horrible accident and Chuck plunged into darkness. He came home when school breaks demanded it and spent all his time shadowing the men in his soon to be company. All the promises he made to his father about protecting his siblings became forgotten and he separated his life from them. He did not even invite the step-family as he called them in his mind at this point to his high school graduation. He invited no one. He felt alone in the world and wanted it to stay that way. Yet, when his name was said as he walked across the stage as he went to receive his diploma he was filled with shock and awe when in the crowd up jumped three blondes. Eric and Serena had steamers, blow horns, and were yelling his name. Even Lily had a sign that proudly declared how proud she was of her son. It was a moment he would never forget. When he greeted after as they hugged him he was surprised to find that Serena had a growth spurt and was almost his height and Eric was no longer a little boy. He saw how much they still looked up to him and he remembered his father's words. 'As their older brother you need to protect them,' his father told him and he renewed the promise to himself.

When he went to Lily a few weeks later he had an entire speech and PowerPoint prepared to convince her to turn the company over to him. She stopped him after about five words and told him the company was his. She trusted him. So they agreed she would help him take the company back if he agreed to a family vacation. Thus, the tradition his father had started but died with him was reborn and the Van der Woodsens and Basses took that special time once a year to regroup. Chuck even moved back into the penthouse for his first year of college not wanting to be lured back into partying since he was busy trying to run a fortune 500 company and earn his degree.

For both Serena and Eric, Chuck was far from perfect but in recent years he became the only male role model in their life. Bart and Lily were only married for four years before he died and they never really knew their father. Whereas Chuck was there for over a decade. Eric was the one who found Monkey and brought him home until Lily discovered an allergy which then Chuck took in Eric's stray. Serena got her fake i.d from Chuck and called him whenever she was too drunk to function. Eric came out first to his brother, learned how to tie a tie and roll a joint from Chuck. When Chuck had his appendix removed they were there at his bedside the whole time with balloons and laughter. With that love sometimes came his over protection. He was in charge of their bank accounts calling them when they withdrew overly large amounts to ensure they were okay. He ran checks on background friends and boyfriends, donated money to the right people to ensure that Serena got into all her schools and Eric was able to get into that photography summer program at the Royal College of the Arts. He had a personal family only cellphone and his assistant knew to always patch his family's call over to him no matter what meeting he was in. Never good with emotions he never hugged or kissed or even told them he loved them but he showed it in every other way he knew how. With money and the things money brought. He was also there for them when they needed a shoulder to lean on. But he never opened up to them. In his mind he was their protector and he needed no protection or guidance from them. They saw him as infallible. The one thing he could count on was being their big brother.

Once Blair came back Chuck made sure not to stare too hard at her. It was clear to him that Serena was suspicious. It was also clear that Blair cared little for the scholarship he created for her benefit making him feel a bit bitter. He was unused to those rebuking his gifts. He was also annoyed that Serena knew about the 'loan' money situation and was not prepared for question. Chuck hated being unprepared. But Blair could not help her glance in his direction. He spoke with his usual indifference and haughty air but his eyes that she remembered being so dark the day they kissed suddenly felt lighter and kinder. Lighter, not in color but in their gaze she thought as she was memorized by the length of his eyelashes that opened up to eyes that she once thought dark and emotionless. It was such a weird thing she thought. Having known him for so long to suddenly see something new about him.

The lunch went off fine and friendly enough. Serena mentioned how her and Blair wanted to go out clubbing this weekend and if could put them down on the V.I.P list on one of his properties. He promised he would and even agree to stop by if he was out and around to stop Serena's pestering. Blair easily laughed around at their sibling banter.

It wasn't until they were leaving that Blair and Chuck finally shared a moment. When the trio emerged from restaurant they found it was lightly snowing and Chuck made it clear he was going to drop them off at school. Serena entered the limo first and Blair was going to enter after her. But Chuck stopped her.

"About the scholarship," he said with annoyance wanting to tell her to forget about applying but she surprised him. She turned around with a full smile on her face and pressed her lips to his lips. By all accounts it was an innocent kiss in the middle of the day in the middle of Manhattan with no sexual intent. It was sweet.

"It is very sweet of you. You, know I am beginning to not believe all the rumors about you being such a womanizer," she teased and Chuck found that suddenly his tongue was dry. How, he wondered could she be so tempting his penthouse and stand here and be so adorable. But he wanted her still. He wanted all of her sweetness and her sauciness.

She turned and entered the town car. Serena was sitting across from her and Chuck entered and sat next to Blair. He was sitting closer than he needed to be but both girls did not notice. None noticed the faint reddish brown lip color that transferred to the edge of Chuck's lower lip on the right corner of his mouth. They were talking freely enjoying the light buzz of the champagne they felt. Chuck stared out the window. He was trying to remember why he was mad, annoyed, or even angry at Blair moments before. She was an enigma to him. More complicated than any woman he ever met.

He exited ahead of them reaching in to grab their hands as they exited always the gentlemen with his sister. He was turning to leave when Blair came fast walking back to him. She left her phone by mistake in the car she realized. But it was only because she was thinking of him while trying to keep up in conversation with her best friend. It was too much to do all that plus remember she placed her phone on the seat next to her.

"I forgot my phone," she said. He wondered if she did on purpose or not.

Reaching in he grabbed it for her but held onto her wrist when she tried to turn back to school.

"You shouldn't have mentioned anything about the loan to Serena without telling me," he told her and she wanted to roll her eyes at him since it was only because he spoken to Nate that Serena found anything out.

"I had to tell her in case my mom thanked her or something next time they meet since she is bound to see her," she easily came up with the solution. Always the quick thinker.

He nodded. "Whatever was supposed to happened or happened is over," he said uncomfortable with the way things were moving with her. Looking over her shoulder he watched the students who left for lunch reenter the building rather than look at her.

Rolling her eyes all she said was "Its over when it's over." Before pulling away and walking away. Chuck ran her words through his mind once more. He grinded his teeth together at how badly he wanted to pull her back and kiss her. The same question rested on both of their minds: Was it really over?

It was not until he was back in his office and his assistant pointed out the reddish brown lipstick smear on his lip. He rubbed the Sugar and Spice lipstick away making him think of Blair for the rest of the day.

* * *

Commentary: Sugar and Spice is the title because of the sweet/spice sides of Blair and her lipstick color. Mainly because we see the sweet side of Blair's personality with a little bit of her sass especially in the coffeehouse. We see the reverse with Chuck she is sweet at first but leaves with a bit of sass at the end. This chapter is finally the last true 'intro' chapter. With the meeting of Scott and the fully flushed Chuck backstory we have a clearer grasp on the characters. Also, I really wanted to add that moment of sweetness with Blair because I find it is the farce/mask she puts on with all the others guys but Chuck. Nate, Marcus, Dan, and the Prince all interact with a Blair that is sweet and intelligent but only Chuck really knows her dark more twisted side. I wanted Blair to have that moment of sweet innocence with Chuck because I wanted to make him react to it. He is usually reacting to girls throwing themselves on him but that peek only last seconds but clearly confuses him.

Also, after this the chapter are going to be going at a much faster pace and the story is picking up. Chuck did tell her to date other people and Blair is fully willing to do that. I mentioned before this story is on the long side so bear with me as it might take a while to get to the fluff that you may want. We have not even scratched the surface of Chuck/Charles persona. They both need a lot of growing before they can be together. Also I fully up to date with my post and drafts so the updates will not be as consistent as I would like.


	7. Guess Who's Coming to Dinner

I have been very busy with family emergencies and have spent much of the last two weeks in the hospital. I had most of this chapter done but very little time to edit everything that I want. But I had two hours of free time to be able to look this over and post. Hopefully, when I look back I won't think it is horrible.

There were so many reviews for the last chapter. I just wanted to thank everyone for all the support. I am sorry to say there is little C/B in this chapter but the next chapter should have plenty. This chapter is pushing the other storylines forward.

To the guest reviewer who wrote about the school-girl crush I would like to thank you for pointing out the much better phrasing that Blair would totally respect and admire Chuck. Which is what I wished to convey. She is not fawning over him but she is aware of his power and his good looks.

Hydridkingbass, Scott has much more of an appearance in this chapter. He is not an OC character so get ready for that. Chuck's background and his relationships with his family is in play in this chapter as well.

* * *

 **Guess Who's Coming to Dinner**

It was Friday in the early evening and Nate was not getting drunk. He needed to finish a paper soon if he wanted to go out to a college party this night with his lacrosse team. He was the captain so he felt pressured to show up but he also needed an A on his paper to save his G.P.A. Instead of any of that he was being driven up to Westchester County. Where the wind was free to howl and blow unrestricted to the wind tunnels that the city skyscrapers created. As a child Nate would love this drive this time of year since he usually marveled at the Christmas decorations that still hung beautifully. Tonight he was busy trying to re-read his essay draft giving no thought to the views.

The town car slowed before stopped in the horseshoe driveway. Nate informed the driver that he could let himself out not seeing the purpose in making the man walk in the cold to open his door. He knew his mother would waited for Armageddon to come before she opened her own door. The Van der Bilt compound was a vast home that the family gathered at for most major functions but usually his grandfather was the only full time resident. It was a soul-sucking mansion. But when you are called you must come. So when Nate's grandfather called and said get in the car Nate got in the car. Half an hour later he had arrived annoyed but ready to face whenever dram his family presented tonight. Briskly he walked to the door only stopping himself to prepared for whatever family issues were going to consume his time. Then he rang the obnoxiously loud doorbell.

Only Tripp and his grandfather sat in the 'small' dining room. The dim chandelier made the rich mahogany look dark and grim. His grandfather rose with a smile, greeted him and announced dinner was to be served. The conversation was light throughout dinner but Nate knew whatever hammer his grandfather was going to drop after dinner. So he waited on edge the entire diner waiting for it to drop.

Back in the city, Chuck was watching the elevator rise making its way to the penthouse floor. Serena mentioned a family dinner on Wednesday he knew it was one he would not want to miss. Lily had not personally invited him but he knew the invitation was always opened so much so that she only served dinner at 6:30 on Fridays on the dot so he could make whether he informed them beforehand or not. Friday was the one day that Bart could be home without fail and Lily had continued their tradition even now.

So Chuck held her favorite bottle of red in his leathered glove hands eager to find out what was troubling his stepmother. When he exited the elevator and rounded the corner he was a bit hurt to see they were all already seated and were at least midway through their meals. Since Lily always served an appetizer and they were consuming entrees he knew that dinner must have started half an hour or more prior.

The tension in the room was thick. He thought his siblings looked pained to be sitting there and he glanced quickly over the other occupants. Taken aback Chuck's eyebrows moved together as if puzzled when he looked at Dan Humphrey then back at Serena who shrugged and then at Lily. He noticed the entire Humphrey family were seated across from his siblings. Jenny was the only one who seemed comfortable in the setting and continued eating.

Lily rose from her seat as she touched the back of her bun in her nervous habit. "Charles, you came for dinner." It was painfully obvious that she was not expecting him. "Rosie, a setting for…" she began but her order trailed off since Rosie, the ever capable help had anticipated the order and had already made a setting for him on the Van der Woodsen side of the table. He was bunched next to Serena.

"I could…" he began to offer to leave but Serena jumped out of her chair and all but begged him to stay with her eyes before he could finish his sentence.

"Please sit," Lily said with a smile and more in control of her surprise.

Jenny quickly began to fill the silence as she talked about the food, the art work in the living room, Christmas in New York, Constance and such. The only one who bothered to speak were Lily, who only answered all the girl's questions with no embellishment, and Eric who was friendly with her at school. Rufus only spoke to mention something about waffles on Christmas as tradition. Chuck, Dan and Serena were silent. Serena and Dan looked at their plates for most of the meal but Chuck surveyed everyone. He wanted to know what this was about. He hated surprises and with every moment that passed he felt the tension building.

Finally, when dessert was served Lily said she had an announcement. The little conversation that was occurring stopped.

"So I know everyone must be wondering why we are all here?" Lily said smiling as she pretended this was not an awkward dinner.

Serena and Dan had dated in high school but he cheated on her secretly for months and then wrote about it in the New Yorker. In response, Blair had cleverly met with the Yale college rep along with some blackmail and some maneuvering made it clear that another boy in Dan's class would get his coveted Yale spot. Dan was now attending Cornell University and had come back to the city solely for this dinner. He was still bitter that he was attending Cornell rather than Yale and partially blamed Serena. Dan held his tongue not wanting to lash out at his former girlfriend. Added to his tension that both Eric and Chuck were shooting dangers at Dan the whole night when he finally spoke with more anger than he intended.

"Are you and my dad dating?" Dan asked his question laced with disgust. But still he voiced the opinion of everyone in the room besides Rufus and Lily.

"No!" Rufus bit and Lily eyed Rufus as if to say 'you wish'.

"No, we wanted to talk to you kids about something. Something we have been hiding from you for a long time," she said as she looked at Dan and Serena clearly concerned over their reactions.

"We dated when we were younger. And…" Rufus said the words dying on his lips as he glanced at Chuck who eyebrows shot up as he realized what they were going to say.

"We had a baby. I was too young to raise and child and CeCe put _him_ up for adoption." Her voice cracked when she said him and her hand quivered a bit as she reached up to touch her bun again. She glanced at Chuck with a smile "He would have been around your age. A few months younger," she said sweetly.

But Chuck's inside twisted. Lily had a son. A son his age. A real biological his age. Eric and Serena had an older brother who was not him.

"We share a sibling?" Serena asked the distaste on her voice as she gestured with her finger between Dan and herself.

It hit Chuck then. Why he was not invited. Everyone in this room shared blood with this missing boy but him. He was alone no biological link to any person here. He swallowed the lump in his throat. The turning of his nerves got worse.

"Do you know his name?" Eric asked with a little more grace than Serena had shown.

"No. The P.I is digging through the records but CeCe was good at covering her tracks and is refusing to help at this point," Lily said with a tight smile.

"Why wait so long to look for him?" Chuck asked betraying his own promise to himself to stay out of it but needing to ask the question.

"Well I wanted to for a long time. I've thought about it forever. I never knew how to tell your father. But when Rufus and I met again when Dan and Serena were….in high school, we talked about. We both decided that when the kids were old enough to understand we would look for him. Eric and Jenny are sixteen this year and felt about right," Lily said speaking to Chuck directly knowing he must still be angry about the early dinner and lack of invitation. She did not mean to exclude him because she did not think he would been as invested in this conversation and she had wanted to talk to him privately about the situation for other reasons.

But for Chuck all he heard was that she thought about her son, her real son all the time. Being almost the same age as her son Chuck let his mind question whether all those moments Lily showed him love and compassion had she pretended that she was showing it to her real son. Easily Chuck's insecurities and the loneliness that pained him pushed him into believing that he was only the replacement son, needed until her real one showed up. But he said nothing and leaned back into his chair as he pretended to be bored by the whole situation.

"This is ridiculous," Serena said throwing down the napkin that was placed on her plate as she stormed off to her room visibly upset. No doubt everyone in the room knew way. Dating your half-brother's half-brother was a bit weird for anyone.

Lily made eyes at her sons hoping that one of them would go see to their sister. Chuck rose ready to go talk to her even though he completely agreed with Serena's statement. However, at the same time Dan rose.

He put his hand out to halt Chuck. "I know what she is going through. Let me try to talk to her… It is weird you know… cause," his voice trailed off as he rubbed the back of his neck not able to meet Chuck's eye any longer. But Chuck nodded letting Dan go with a stern glance to serve as a warning.

With Dan and Serena gone from the room and Eric and Jenny pretending to be excited as they asked their parents for information. Chuck suddenly felt a bit lonely in the penthouse that he considered home above any other location. Feeling dejected he stood to leave.

"I need to be off. Thank you for a lovely night, Lily. Of course let me know if you need any help at all locating your _son,"_ his greeting was said stiffy without emotion. Lily raised an eyebrow out of concern and stood to walk with Chuck to the elevator.

"Chuck, I am sorry I needed to start dinner earlier than usually. Dan needs to head back to Cornell tonight," she said in way of explaining but gave no explanation as to way she would have not informed him of the change of time considering the significance of the dinner.

Nodding; he quickly walked out of the dining room to the elevator not wanting to have any conversation. But Lily, hot on his heels, followed him out knowing she needed to say something.

"I would like to talk to you about all this Chuck. There is more to this…" she said trying to catch his eye to figure out what he was thinking. But he was dodging her gaze as he busied himself with putting on his coat and gloves.

Finally meeting her gaze. "About your son?" he asked his voice bitter. He was cursing at himself internally for displaying so much emotions.

"No, about you. All this talk of long lost family. There is something that you must know about your mother. Something I should have told you years ago," She placed her hand on his wrist as a show of comfort. But an icy chill ran through Chuck's body instead.

"My mother is dead," he shot back. That was a fact, he thought. But maybe the long lost relatives were her family members or something. He could not help but wonder if perhaps out there somewhere in the world someone was walking around with the same blood as him. A family relative. Someone anyone out there with some ties to himself. Someone who was not as scheming and cruel as his uncle Jack.

At that moment an excited Jenny and Eric came rolling into the foyer. "Mrs. Bass, Eric and just had the greatest idea. We should throw him a surprise party when we all meet. A family party," she gushed. The words came back hitting Chuck. He knew on some level the girl was just excited to be somehow related to the UES famous Rhodes/Van der Woodsen clan. He was only related by his dead father.

"We will talk later," he whispered to Lily before leaving. He needed to get out of this place. She nodded sadly at him and then turned to addressed Jenny and Eric.

The long way down the elevator left Chuck feeling more like an outsider than he ever had before. Needing a release through women, booze, and maybe some dope he called Nathaniel. But there was no answer.

Nate saw the call but hit ignore since he was trying to process what his grandfather and Tripp wanted. He knew it would be better if he did not pause the conversation to talk to the man that his grandfather suddenly seemed so obsessed with.

"Tripp is down by a lot in the polls. I am unsure how me bringing Chuck in is going to help with his run," Nate said as he put his phone back into his pocket hoping Chuck would not call again.

"He is a billionaire. Don't be such a fool as to question why that matters. We need the money. The donations have dried up," his grandfather berated him as he sipped from his glass of scotch. Nate eyed the brown liquid in his glass. He was never a scotch man. Not like his grandfather and Chuck. He much rather preferred gin and maybe a beer every now and then.

"I am pretty sure he is a Republican," he said shrugging wanting to pretend this was not a big deal.

He thought it was ironic since he was pretty sure that if his grandfather was not a part of the New York political machine he would be undoubtable a Republican as well. Political parties meant nothing to the Van der Bilts. Power was the only thing that mattered. But with the increasing cost of running political campaigns even small ones the cost added up. Between the TV ads, online ads, radio ads, newspaper editorials, and social media presence in a district with twelve million people it cost a hell of a lot of money. Being in the spotlight in New York meant national attention and national attention meant name recognition which was half the battle in Presidential and State primaries. His grandfather of course knew all of this of course which was why he wanted one of his two grandsons to become mayor of New York City eventually.

"It is a two-pronged attack. We need dirt on Luther Mulligan and we need money for ads. Charles can help us with both," Tripp said as he basically repeated his grandfather's words from dinner.

Luther Mulligan was the U.S Attorney for the Southern District of New York who was only running in a non-winnable seat for a Republican in order to make a play for governor next year. Mulligan was a hardline pick up yourself by your bootstraps conservative who was running a moral campaign. Everyone who knew him thought him fair but ruthless. Nate wanted to laugh. The entire that Mulligan would have an ounce of dirt to be hidden was heard to believe. Plus, even Tripp knew how much Chuck hated his cousin and he doubted he would give him a cent but ever the negotiator Nate did not want to be so bluntly rude.

"Why would he even have dirt on Mulligan?" Nate asked as he shifted in his seat before bringing the glass that was still half full to his lips.

"Back when Mulligan was an AUSA he had a RICO case against the Mob back a decade or so ago. The crimes were for things going back into the early 90s. Back in the eighties, with Bart being young in the real estate business and the nature of the city in those years you had to be in bed with the mob. No way around it and Bart knew how to play the game. So when the RICO trial came up Bart's name was on the original arrest warrant list. From the way I hear things Bart had some serious blackmail on the man and got that warrant to disappear. I have never seen that son of a bitch back down from anything like that. What I understand about both the they kept their blackmail material always close at hand. We need what Bart had," William said. His eyes drifted off as he spoke as he remembered the old days of politics. When his political machine was strong and both the Gracie Mansion and the New York State Executive Mansion were under his control. Then a fierce determined look washed over him as glanced back at Nate. Suddenly, Nate became nervous under that glare as if his own grandfather would rip him apart if Nate stood in his way of his ultimate goal.

Running a nervous hand over his face, Nate took a deep breath as he silently asked God or the universe why was he in this family. Certainly Nate loved politics as much as his grandfather did but for all the different reasons. While his grandfather wanted him and Tripp to be the next Bobby Kennedy and John F. Kennedy with all the fame and power, all Nate wanted was to have a long distinguished career as a liberal like Ted Kennedy. He cared a strong sense of morality and duty to help those less fortunate than himself. But he knew politics was a game of deceit and in that arena no one was more valuable to him then his grandfather.

"Okay I will talk to him," Nate said hoping the conversation and this evening was near an end.

"Talk! Nate we need this to work. Maureen needs me to win," Tripp said in anger. Maureen did not need him to win. Tripp needed Tripp to win.

"How is Maureen?" Nate asked to change the conversation.

Tripp did not answer for a moment as his back was turned to Nate while he poured himself more of a drink. Nate glanced at his own glass to see it was still a finger left of liquid. He was going slow tonight. He liked to keep a clear head around his family.

"She behaving. Your mother is a god send. She has her acting, talking, and thinking right." Nate's stomach clench at the thought and he quickly threw back the alcohol deciding he needed to be a bit drunk. Standing up to get more as Tripp sat down. "She really understands the way that Maureen needs to act to be a _good wife_."

Nate wanted to smack his cousin a few times for that comment and remind him that he was the one cheating on his wife. But there was also that sickening feeling of knowing that Tripp was right. A women married to a politician needed to be a politician herself. There was no doubt an aura and persona that wife must display. His mother raised by her cold father always played the part so well. There was no doubt that Anne would have been a ruthless business women, lawyer, or politician herself but she was raised to never really work. It was a different thoughts drifted to Serena trying to picture her at his side. Serena was so different. He could never picture her wanting that life.

"I'm happy she is feeling better," Nate said with dryly since not once did his cousin actually mention his how his wife was feeling.

"Nate, Tripp is making a good point here about a wife. Have you thought of taking one," William said. Nate squeezed the glass in his hand to stop him from screaming out. Their disregard for anyone not there to help their plans was giving him a horrible headache.

"I hardly think it is relevant to his conversation," Nate said smoothly.

"Well you should be thinking about it. I had internal polling done and we found you are best suited for a girl who comes from a blue collar family and/or a minority girl. Even better if she is from the rust belt," Willian said off handedly. Nate glared at him but said nothing. Not wanting to have this discussion yet again. His grandfather had mentioned this to him before and they had a fierce argument. No doubt William thought polling would sway Nate's mind.

"Stop it," was all Nate gritted out. Since he had the leverage at the moment through his relationship with Chuck that they were desperate for William Van der Bilt for once bit his tongue and said no more.

Back in the city, Blair was finishing up dinner with Scott. They had grabbed a bite to eat at a Thai restaurant in SOHO and were headed to see a French Film at the IFC center. For Blair it was unlike any date she would have pictured herself at. The food was mediocre, Scott didn't even wear a dinner jacket or tie, and he did not refuse her when she offered to pay half the bill. Despite all these reasons that she thought she would hate she found that she was actually having a good time. Never before had she thought her intelligence to be an attractive trait but Scott continued to compliment her and her knowledge of art, movies, and culture. She found herself having a real conversation about a dozen different topic with him never once was there an awkward silence. Maybe it was the feminist in her but the dinner was so different than that with Chuck. With Chuck she felt like a piece of the meal at dinner and with Scott she felt like a person. After dinner the two were planning on seeing a Éric Rohmer film.

"I love the French New Wave films. There is something so fresh and refreshing," Blair said as she walked along with Scott. It was cold out and the streets were emptier than normal.

"So true. I think they are playing one of Rohemer season films. I think the summer one and if I remember correctly it doesn't have a soundtrack. But there are these birds on the beach, seagulls that croak so loud sometimes and I remember thinking it was so refreshing and different. It makes it feel real in a way that engineered sounds don't do," Scott said.

"Well there goes your career plan," she joked with him giving him a teasing smile.

He laughed and then went on to explain how he wanted to be in charge of the music that creates a scene and conveys emotions but admitted that the sometimes it was unnecessary. "It is always best used correctly but some of the time it could be overdone which makes the viewer ignore the subtle changes that music can convey," he said and she followed along commenting her thoughts which he seemed to appreciate. They were nearing the theater when the Scott stopped and give Blair the bag he was holding. He had it with him at dinner and had told her it was a surprise.

Peeking into the bag Blair smiled widen when she saw it was macaroons from Ladurée. One of her favorite New York bakeries.

"My favorite," she said a bit surprised but elated that he did this.

"You mentioned it at the coffeehouse and I figured a French film deserves a French dessert."

"How sweet," she said before he reached down to kiss it. It was a merely a touch of lips for their first kiss. Pulling back, he looked at her smiling and she smiled back. Unable to stop herself she compared his fleeting kiss to Chuck's demanding one. It was unfair, she thought, to compare because they were vastly different people. Then she began to think about herself. Who was she more like cultured plain Scott or ruthless brilliant Chuck? Who was Blair Waldorf going to be and who did she want?

* * *

Guess Who's Coming to Dinner is the name of two famous Hollywood movies and since most of the characters are seen at dinner or after dinner. In this chapter, the guessing is who missing from the Van der Woodsen dinner. If you are a fan of the show you should at this point be aware of who Lily and Rufus's son is. I am surprise no one guess this earlier and I never intended this to be that much of surprise but I think it might be for some so I won't come right out and say it.

So Scott and Blair's first date was never supposed to be written. It just kind of popped into my mind because I thought I should show Blair and Scott's relationship before the jealous Chuck and Scott scene. It helps create that Scott/Chuck binary.

Chuck is feeling very isolated and is hurt by Lily's secret child. We see that he feels alone in the world a bit since he has no blood ties to his closest relatives. As close as he is with the Van der Woodsen he feels replaced by Lily's 'real son'. FYI, Uncle Jack plays a very small role in this story and does not have a close relationship with Chuck.

Also, for those wondering or unfamiliar with (The Racketeer Influenced and Corrupt Organizations Act) **RICO** it is a federal law that allows for the prosecution for racketeering against a group of people for an ongoing criminal ring (family). The seventies, eighties and earlier nineties in New York were really embedded with organized crime in a way that is very different than now so I think it would be plausible that Bart would have gotten involved with them. Also, an **AUSA** (Assistant U.S Attorney) which Mulligan's character was but is now a U.S federal Attorney. This is a position that is appointed by the U.S president which in this timeline is going to change because the president is newly elected. The governor's race in New York would take place in 2010. I think I explained everything. If there are any questions let me know. The **Rust Belt** is the area were the declining Steel-producing cities in state such as Pennsylvania, Ohio and other cities in the upper North-Eastern United States, the Great Lakes, and the Midwest States.


End file.
